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

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

Uses

Used in Pharmaceutical Industry:
(+)-4'-Chlorotartranilic Acid is used as a chemical intermediate for the development of approved drugs and bioactive molecules. Its chlorinated tartrate structure contributes to the pharmaceutical industry by providing a foundation for the synthesis of various medicinal compounds.
Used in Chemical Synthesis:
(+)-4'-Chlorotartranilic Acid is used as a key component in the synthesis of other chemical substances. The importance of chlorinated derivatives in chemical reactions makes this compound a valuable asset in the production of a range of chemical products.

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

• 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 
• 608141-41-9 Apremilast 

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.

Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.

The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.