Ammonia → HCID 66882216, compound

HRID 1968718Notes

Reaction equation

HRID 1968718 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16][N:17]([CH3:19])[CH3:18])[CH:9]=[N:10]2.[NH3:21]>CO>[Cl:15][C:14]1[C:5]([CH2:4][C:3]([NH2:21])=[O:2])=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([CH2:16][N:17]([CH3:19])[CH3:18])=[CH:7]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66881101HCID 66881101, compound

Product 1

HCID 66882216HCID 66882216, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (6-chloro-3-dimethylaminomethyl-quinolin-5-yl)-acetic acid methyl ester (462 mg, 1.58 mmol) in a mixture of methanol (4 mL) and liquid ammonia (20 mL) was stirred for 4 days in an autoclave at room temperature. After careful evaporation of the ammonia, the remaining solvent was evaporated in vacuo to afford the title compound as a pale brown solid (413 mg, 1.48 mmol, 94%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=8.85 (d, J=2.0 Hz, 1H), 8.31 (bs, 1H), 7.93 (d, J=9.1 Hz, 1H), 7.75 (d, J=9.1 Hz, 1H), 7.62 (bs, 1H), 7.08 (bs, 1H), 4.10 (s, 2H), 3.67 (bs, 2H), 2.23 (bs, 6H). MS (ES+): 278 (M(C14H1635ClN3O)+H)+.

Workup

  1. customAfter careful evaporation of the ammonia
  2. customthe remaining solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1b7807230e7540c888f4b6d2774da5f0
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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