72299-67-3

Basic information

• Product Name: 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• Synonyms: 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;1,2,3,4-TETRAHYDROISOQUINOLIN-6-AMINE;1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-YLAMINE;1,2,3,4-Tetrahydro-6-isoquinolinaMine;6-AMino-1,2,3,4-tetrahdyroisoquinoline
• CAS NO: 72299-67-3
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• Product Categories: pharmacetical;Quinoline series
• Mol File: 72299-67-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 315.903°C at 760 mmHg
• Flash Point: 169.23°C
• Appearance: Off-white/
• Density: 1.101g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.17±0.20(Predicted)
• CAS DataBase Reference: 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(72299-67-3)
• EPA Substance Registry System: 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(72299-67-3)

Safety Data

• Hazardous Substances Data: 72299-67-3(Hazardous Substances Data)

Usage

General Description

6-Amino-1,2,3,4-tetrahydro-isoquinoline is a chemical compound with the molecular formula C9H12N2. It is a derivative of isoquinoline, a heterocyclic compound with a six-membered ring structure containing nitrogen and carbon atoms. The presence of an amino group in the molecule makes it a basic compound and it can act as a ligand in coordination chemistry. 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE has potential applications in pharmaceutical research and drug development due to its structural similarity to biologically active compounds. Its unique molecular structure and potential reactivity make it a subject of interest in organic and medicinal chemistry studies for its potential therapeutic effects.

InChI:InChI=1/C9H12N2/c10-9-2-1-8-6-11-4-3-7(8)5-9/h1-2,5,11H,3-4,6,10H2

Synthetic route

1,2,3,4-tetrahydroisoquinolin-6-amine dihydrobromide → 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

Conditions	Yield
With sodium hydroxide In water	100%

6-isoquinolinamine (23687-26-5) → 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol; water Flow reactor; Heating;	99%

6-amino-3,4-dihydro-isoquinoline-1(2H)-one (22246-00-0) → 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Reduction; Heating;	0.6 g

6-isoquinolinamine (23687-26-5) + tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9) + 3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone → 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

7-nitro-1,2,3,4-tetrahydroisoquinoline (42923-79-5) + 6-nitro-1,2,3,4-tetrahydro-isoquinoline (186390-77-2) → 1,2,3,4-Tetrahydro-isoquinolin-7-ylamine (72299-68-4) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

Conditions	Yield
With iron; ammonium chloride In ethanol; water at 60℃; for 24h;

tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9) → 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 1.5h;	4.85 g

di-tert-butyl dicarbonate (24424-99-5) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (164148-92-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; under 7500.75 Torr; Flow reactor;	91%
In tetrahydrofuran; water at 20℃; for 3h;	73%
In tetrahydrofuran at 20℃; for 3h;	73%

bromoacetic acid tert-butyl ester (5292-43-3) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 6-amino-1,2,3,4-tetrahydroisoquinolineacetic acid 1,1-dimethylethyl ester (252061-95-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 24h; Condensation;	70%

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 6-[(4-cyanobenzoyl)amino]-1,2,3,4-tetrahydroisoquinolineacetic acid 1,1-dimethylethyl ester (164148-93-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / K2CO3 / acetonitrile / 24 h / 20 °C 2: 60 percent / (1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide)*HCl; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 6-[[4-[[[(1,1-dimethylethoxy)carbonyl]amino]iminomethyl]benzoyl]amino]-1,2,3,4-tetrahydroisoquinolineacetic acid 1,1-dimethylethyl ester (164148-94-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / K2CO3 / acetonitrile / 24 h / 20 °C 2: 60 percent / (1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide)*HCl; DMAP / CH2Cl2 / 12 h / 20 °C 3: 0.34 g View Scheme

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 6-[[[4-(aminoiminomethyl)phenyl]carbonyl]amino]-1,2,3,4-tetrahydroisoquinolineacetic acid trifluoroacetate

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / K2CO3 / acetonitrile / 24 h / 20 °C 2: 60 percent / (1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide)*HCl; DMAP / CH2Cl2 / 12 h / 20 °C 3: 0.34 g 4: 3 h / 20 °C View Scheme

1,2,3,4-Tetrahydro-isoquinolin-7-ylamine (72299-68-4) + 2,3-dimethyl-N-(2-chloropyrimidin-4-yl)-N-methyl-2H-indazole-6-amine (444731-75-3) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → N4-(2,3-dimethyl-2H-indazol-6-yl)-N4-methyl-N2-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidine-2,4-diamine hydrochloride + N4-(2,3-dimethyl-2H-indazol-6-yl)-N4-methyl-N2-(1,2,3,4-tetrahydroisoquinolin-6-yl)pyrimidine-2,4-diamine hydrochloride

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol Heating / reflux;

(Pyridin-3-yloxy)-acetic acid (86649-57-2) + 1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 1-(6-amino-3,4-dihydro-1H-isoquinolin-2-yl)-2-(3-pyridyloxy)ethanone

Conditions	Yield
Stage #1: (Pyridin-3-yloxy)-acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 45℃; for 1h; Inert atmosphere; Stage #2: 1,2,3,4-tetrahydroisoquinolin-6-amine In tetrahydrofuran; N,N-dimethyl-formamide for 2h; Inert atmosphere;	8.87 g

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → tert-butyl 4-[[2-[2-(3-pyridyloxy)acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]sulfamoyl]piperidine-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: triethylamine / dichloromethane / 3.5 h / 20 °C View Scheme

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → N-[2-[2-(3-pyridyloxy)acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]piperidine-4-sulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: triethylamine / dichloromethane / 3.5 h / 20 °C 3.1: hydrogenchloride / dichloromethane; water / 17 h / 20 °C View Scheme

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → 1-(oxetan-3-yl)-N-[2-[2-(3-pyridyloxy)acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]piperidine-4-sulfonamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: triethylamine / dichloromethane / 3.5 h / 20 °C 3.1: hydrogenchloride / dichloromethane; water / 17 h / 20 °C 4.1: dichloromethane / 1 h / 20 °C 4.2: 20 °C View Scheme

1,2,3,4-tetrahydroisoquinolin-6-amine (72299-67-3) → N-[2-[2-(3-Pyridyloxy)acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]-1-(tetrahydropyran-4-carbonyl)piperidine-4-sulfonamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: triethylamine / dichloromethane / 3.5 h / 20 °C 3.1: hydrogenchloride / dichloromethane; water / 17 h / 20 °C 4.1: triethylamine / dichloromethane / 0.5 h 4.2: 0.5 h / 0 °C View Scheme

Upstream product

• 22246-00-0 6-amino-3,4-dihydro-isoquinoline-1(2H)-one 
• 42923-79-5 7-nitro-1,2,3,4-tetrahydroisoquinoline 
• 186390-77-2 6-nitro-1,2,3,4-tetrahydro-isoquinoline 
• 23687-26-5 6-isoquinolinamine 
• 164148-92-9 tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Downstream Products

• 164148-93-0 6-[(4-cyanobenzoyl)amino]-1,2,3,4-tetrahydroisoquinolineacetic acid 1,1-dimethylethyl ester 
• 164148-94-1 6-[[4-[[[(1,1-dimethylethoxy)carbonyl]amino]iminomethyl]benzoyl]amino]-1,2,3,4-tetrahydroisoquinolineacetic acid 1,1-dimethylethyl ester 
• 164148-92-9 tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 

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