Acetic Anhydride → 4-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 2109866Notes

Reaction equation

HRID 2109866 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][C:2]1=[O:11].C(N(C(C)C)CC)(C)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>ClCCl>[C:21]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][C:2](=[O:11])[CH2:3]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-

Product 1

HCID 27708254-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 3,4-dihydroquinoxalin-2(1H)-one (1.0 g, 6.7 mmol; J. Med. Chem. 758, 1994) and N,N-diisopropyl-N-ethylamine (1.7 mL, 10.1 mmol) in dichloromethane (30 mL) under an atmosphere of nitrogen, acetic anhydride (0.76 mL, 8.1 mmol) was added and stirred at room temperature overnight. The resultant solution was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 1% methanol in chloroform. Collection and concentration of appropriate fractions provided the acetylation product.

Workup

  1. concentrationThe resultant solution was concentrated under vacuum
  2. customCollection and concentration of appropriate fractions
  3. customprovided the acetylation product

Sources & evidence

ORD record
ord-a03f1253aa264c2c937df899681758bf
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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