Ammonium Hydroxide → 6-Iodo-4-methoxy-quinoline-3-carboxylic acid amide

HRID 1297611Notes

Reaction equation

HRID 1297611 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([I:17])=[CH:10][CH:9]=2)=O.[OH-].[NH4+:19]>>[I:17][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([C:3]([NH2:19])=[O:2])=[C:14]2[O:15][CH3:16]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 688283896-Iodo-4-methoxy-quinoline-3-carboxylic acid methyl ester

Product 1

HCID 688249156-Iodo-4-methoxy-quinoline-3-carboxylic acid amideYield 88%

Conditions

Temperature
150 °C

Procedure

A suspension of 6-iodo-4-methoxy-quinoline-3-carboxylic acid methyl ester (example 1d) (1.7 g, 5 mmol) in ammonium hydroxide (28%, 75 mL) was heated at 150° C. for 4 days under pressure tube. After cooling, the solvent was removed by rotary evaporator. The solid was collected by filtration, washed with water and dried to obtain 6-iodo-4-methoxy-quinoline-3-carboxylic acid amide (1.4 g, 88%) as a black solid. LC-MS m/e 329 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by rotary evaporator
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2f38e0b650bb42c5b9f11706c72b5271
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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