Acetic Anhydride → N-{4-[(3-Bromophenyl)amino]-3-cyano-8-dimethylaminomethyl-6-quinolinyl}acetamide

HRID 1934977Notes

Reaction equation

HRID 1934977 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[N:8]=[CH:7][C:6]([C:16]#[N:17])=[C:5]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(O)(=O)C>[Br:25][C:21]1[CH:20]=[C:19]([NH:18][C:5]2[C:4]3[C:9](=[C:10]([CH2:12][N:13]([CH3:14])[CH3:15])[CH:11]=[C:2]([NH:1][C:26](=[O:28])[CH3:27])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:16]#[N:17])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 101353526-Amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrile

Product 1

HCID 10296862N-{4-[(3-Bromophenyl)amino]-3-cyano-8-dimethylaminomethyl-6-quinolinyl}acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 6-amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrile (0.20 g, 0.50 mmol) and 1.5 ml of acetic acid at 25° C. was added 0.14 ml (1.5 mmol) of acetic anhydride. After 60 m volatile matter was evaporated off under vacuum. The residue was stirred with sodium bicarbonate solution. The resulting solid was filtered off, washed with water, dried, and recrystallized from isopropanol-hexane to give a light yellow solid, mp 162-167° C.

Workup

  1. customAfter 60 m volatile matter was evaporated off under vacuum
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from isopropanol-hexane
  6. customto give a light yellow solid, mp 162-167° C.

Sources & evidence

ORD record
ord-4afe290a9b084940a0481d9c5e69c80d
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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