Hydrochloric Acid → 2,3-Dimethyl-7-indolecarboxylic acid

HRID 1835484Notes

Reaction equation

HRID 1835484 reaction equation
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])N.[CH3:13][C:14](=O)[CH2:15][CH3:16].Cl>C(O)(=O)C.O>[CH3:13][C:14]1[NH:2][C:4]2[C:12]([C:15]=1[CH3:16])=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6569Methyl Ethyl KetoneHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)

Product 1

HCID 37026102,3-Dimethyl-7-indolecarboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-hydrazinobenzoic acid hydrochloride (2.0 g) in acetic acid (8 ml) was added dropwise a solution of 2-butanone (0.9 ml) in acetic acid (2 ml), and the resultant mixture was heated at 80° C. for one hour. After 6N-hydrochloric acid (8 ml) was added to the reaction mixture, the mixture was heated at 100° C. for 5 hours. The mixture was diluted with water (18 ml), and allowed to cool to 40° C. The resultant precipitate was collected by filtration, washed with a small amount of diisopropyl ether and dried in vacuo to give 2,3-dimethyl-1H-indole-7-carboxylic acid (0.78 g).

Workup

  1. temperatureto cool to 40° C
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with a small amount of diisopropyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b41d1493bb0c4115a8f24ee0cca85767
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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