Acetic Anhydride → N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-acetamide

HRID 1422232Notes

Reaction equation

HRID 1422232 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2.BrCC1C=C([N+]([O-])=O)C=C2C=1N=[C:25](OC)[C:26]([O:35]C)=N2.C(OC(=O)C)(=O)C.C(N(CC)CC)C>C(N(CC)C=O)C.C(OCC)C>[CH3:17][O:16][C:7]1[C:6]([O:18][CH3:19])=[N:5][C:4]2[C:9](=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[CH2:2][NH:1][C:26](=[O:35])[CH3:25])[N:8]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxalineHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 18706427N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-acetamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 12051DiethylformamideSolvent

Procedure

111 mg (0.437 mmol) of 5-aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline, obtainable in a manner analogous to that described in Example 9 but starting from 5-bromomethyl-2,3-dimethoxy-7-nitro-quinoxaline, are stirred with 0.046 ml (1.1 equiv.) of acetic anhydride and 0.073 ml (1.2 equiv.) of triethylamine in 5 ml of N,N-diethylformamide at room temperature for 24 hours. The reaction mixture is diluted with diethyl ether, and the solid is filtered off, washed with diethyl ether and dried.

Workup

  1. filtrationthe solid is filtered off
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-390f1566680049a9818d0fcf93d57184
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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