Acetic Anhydride → 6-Acetamido-2-methoxy-8-methylquinoline

HRID 568383Notes

Reaction equation

HRID 568383 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[N:15]=[C:14]([O:20][CH3:21])[CH:13]=[CH:12]2>ClCCl>[C:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[N:15]=[C:14]([O:20][CH3:21])[CH:13]=[CH:12]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 198670716-Amino-2-methoxy-8-methylquinoline

Product 1

HCID 198670766-Acetamido-2-methoxy-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of acetic anhydride (0.55 cm3) in dichloromethane (20 cm3) was added dropwise to a stirred solution of 6-amino-2-methoxy-8-methylquinoline (1.0 g) in dichloromethane (30 cm3) at room temperature. After 1 hour the solution was diluted with dichloromethane (50 cm3), washed with saturated sodium carbonate solution (10 cm3), and dried (MgSO4). Evaporation of the solution in vacuo afforded a solid which was recrystallised from dichloromethane/hexane to give 6-acetamido-2-methoxy-8-methylquinoline, m.p. 193°-196° (1.143 g).

Workup

  1. washwashed with saturated sodium carbonate solution (10 cm3)
  2. dry with materialdried (MgSO4)
  3. customEvaporation of the solution in vacuo
  4. customafforded a solid which
  5. customwas recrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-fb1b9f13e26247218d0740679c188e98
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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