17447-35-7

Basic information

• Product Name: (+)-4'-CHLOROTARTRANILIC ACID
• Synonyms: L-TACA;L-TARTARIC ACID MONO-P-CHLOROANILIDE;(+)-4'-CHLOROTARTRANILIC ACID;(R,R)-4'-Chloro-tartranilic acid;(2R,3R)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid
• CAS NO: 17447-35-7
• Molecular Formula: C₁₀H₁₀ClNO₅
• Molecular Weight: 259.64
• Mol File: 17447-35-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 609.1°Cat760mmHg
• Flash Point: 322.2°C
• Appearance: /
• Density: 1.644g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-4'-CHLOROTARTRANILIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-4'-CHLOROTARTRANILIC ACID(17447-35-7)
• EPA Substance Registry System: (+)-4'-CHLOROTARTRANILIC ACID(17447-35-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 17447-35-7(Hazardous Substances Data)

Usage

General Description

"(+)-4'-Chlorotartranilic Acid" is a chemical compound known for its applications in organic chemistry and pharmaceutical studies. Though detailed information about its specific usage is limited, it is recognized as a type of chlorinated tartrate, a group of chemicals commonly used in developing approved drugs and bioactive molecules, potentially contributing to the pharmaceutical industry. Furthermore, this compound could also be relevant in producing other chemical substances, given the significance of chlorinated derivatives in chemical synthesis. Basic chemical information suggests it contains chlorine and is acidic in nature. However, it is important to consider the need for safety measures in handling such chemicals due to possible hazardous effects.

Synthetic route

4-chloro-aniline (106-47-8) + (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate (6283-74-5) → (R,R)-(+)-4-chlorotartranilic acid (17447-35-7)

Conditions	Yield
In dichloromethane for 15h; Heating;	68%

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (253168-94-4) + (R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → C12H19NO4S*C10H10ClNO5

Conditions	Yield
With hydrogenchloride In water at 60 - 70℃; Solvent; Resolution of racemate; Heating;	92%

3-hydroxypiperazine (6859-99-0) + (R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → (2R,3R)-N-(4-Chloro-phenyl)-2,3-dihydroxy-succinamic acid; compound with (R)-piperidin-3-ol

Conditions	Yield
In ethanol at 40℃;	74%

(+/-)-5-(4-amino-3-methylphenyl)-8-methyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (943964-30-5) + (R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → (S)-(-)-5-(4-amino-3-methylphenyl)-8-methyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine salt with L-tartaric acid semi-4-chloroanilide (943964-32-7)

Conditions	Yield
In ethanol at 20℃; for 20h; Heating / reflux;	36%

(R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → Apremilast (608141-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 60 - 70 °C / Resolution of racemate; Heating 2: acetic acid / 24 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: chloroform / Heating; Resolution of racemate 2: acetic acid / 24 h / Reflux View Scheme

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (253168-94-4) + (R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → C12H19NO4S*C10H10ClNO5 + C12H19NO4S*C10H10ClNO5

Conditions	Yield
In chloroform Solvent; Heating; Resolution of racemate; Overall yield = 94 %;	A n/a B n/a

Upstream product

• 106-47-8 4-chloro-aniline 
• 6283-74-5 (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate 

Downstream Products

• 608141-41-9 Apremilast 
• 943964-32-7 (S)-(-)-5-(4-amino-3-methylphenyl)-8-methyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine salt with L-tartaric acid semi-4-chloroanilide 

Relevant articles and documents

METHOD FOR OBTAINING AN OPTICALLY PURE 1,2,3,4 TETRAHYDRO-ISOQUINOLINE DERIVATIVE

The invention relates to a method for obtaining enantiomerically enriched 6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline from a mixture of (R)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline and (S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline.