Acetic Anhydride → N-(6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoxalin-9-yl)-acetamide

HRID 863490Notes

Reaction equation

HRID 863490 reaction equation
[NH2:1][CH:2]1[CH2:20][C:6]2[C:7]3[NH:8][C:9](=[O:19])[C:10](=[O:18])[NH:11][C:12]=3[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:5]=2[CH2:4][CH2:3]1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)CC)C>CN(C)C=O>[N+:15]([C:14]1[C:5]2[CH2:4][CH2:3][CH:2]([NH:1][C:21](=[O:23])[CH3:22])[CH2:20][C:6]=2[C:7]2[NH:8][C:9](=[O:19])[C:10](=[O:18])[NH:11][C:12]=2[CH:13]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 196962049-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

Product 1

HCID 19696211N-(6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoxalin-9-yl)-acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione (0.15 g, 0.5 mmol), acetic anhydride (0.1 g, 1 mmol) and triethylamine (0.2 g, 2 mmol) in dimethylformamide (5 mL) was stirred at room temperature for 3 h. The solvent was removed by rotoevaporation, and the residue suspended in water and 2N HCl. The solid which formed was collected by filtration, washed with diethyl ether and dried to give the acetamide (0.14 g) in 88% yield. Anal. calc'd for C14H14N4O5.H2O: C, 50.00; H, 4.80; N, 16.66; found-C, 49.92; H, 4.77; N, 16.04.

Workup

  1. customThe solvent was removed by rotoevaporation
  2. customThe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-3d95a8f8165846d785da2d3bb0834cfe
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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