Acetic Anhydride → 7-(Acetylamino)-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide

HRID 2289913Notes

Reaction equation

HRID 2289913 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:23])=[C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1.O>[C:24]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:23])=[C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 178507324HCID 178507324, compound

Product 1

HCID 1784740467-(Acetylamino)-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 100 mg of 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide in 1 mL of anhydrous pyridine is treated with 0.032 mL of acetic anhydride. After 24 h, an additional 0.005 mL of acetic anhydride is added and the mixture is stirred for an additonal 48 h. The mixture is diluted with 2 mL of distilled water and the precipitate is collected by filtration. It is washed with two 1 mL portions of distilled water and dried in a stream of air. It is dried at 20 torr/75°C./16 h. The product is obtained as 78 mg of a tan solid.

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washIt is washed with two 1 mL portions of distilled water
  3. customdried in a stream of air
  4. customIt is dried at 20 torr/75°C./16 h

Sources & evidence

ORD record
ord-c4d215c891264b4ebdaf88de5835b42d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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