Acetic Anhydride → HCID 10249934, compound

HRID 1885175Notes

Reaction equation

HRID 1885175 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH3:26])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:27](=[O:29])[CH3:28])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH3:26])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11725437HCID 11725437, compound

Product 1

HCID 10249934HCID 10249934, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinoline (1.75 g, 5 mmol) was dissolved in a mixture of acetic anhydride (10 ml) and pyridine (10 ml), stirred for 18 hours at room temperature, then the solvent evaporated, the product dissolved in dichloromethane and washed with aqueous sodium bicarbonate. Dryinq, evaporation, and recrystallisation from ethyl acetate/petroleum ether gave 3-butyryl-4-(4-acetoxy-2-methylphenylamino)-8-methoxyquinoline (1.55 g, 79%), m.p. 167°-169°.

Workup

  1. customthe solvent evaporated
  2. dissolutionthe product dissolved in dichloromethane
  3. washwashed with aqueous sodium bicarbonate
  4. customDryinq, evaporation, and recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-8c50098c108144988337f14437723439
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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