Hydrochloric Acid → 5-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamide

HRID 2091185Notes

Reaction equation

HRID 2091185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.[CH3:15][NH:16][O:17][CH3:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:16]([O:17][CH3:18])[CH3:15])=[O:13])=[CH:5]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 230033115-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamideYield 84.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-chloro-1H-indole-2-carboxylic acid (15.0 g), N,O-dimethylhydroxylamine hydrochloride (8.97 g), 1-hydroxybenzotriazole monohydrate (14.1 g), triethylamine (25.6 mL) and N,N-dimethylformamide (200 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (17.6 g), and the mixture was stirred overnight at room temperature. 1N Hydrochloric acid was added to quench the reaction, the resulting precipitate was collected by filtration to give the title object compound (15.5 g, 84%) as a pale-brown solid.

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-5db922d5342342ba9b2af105b6cf89b4
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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