Acetic Anhydride → 2-(6-acetamido-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazin-4-yl)pyridine N-oxide

HRID 37111Notes

Reaction equation

HRID 37111 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=3[O-:19])[C:6]=2[CH:20]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=3[O-:19])[C:6]=2[CH:20]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 152917732-(6-amino-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazin-4-yl)pyridine N-oxide

Product 1

HCID 158572142-(6-acetamido-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazin-4-yl)pyridine N-oxide

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

To a solution of 0.474 g of 2-(6-amino-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazin-4-yl)pyridine N-oxide in 5 ml of acetic anhydride was added 3 drops of pyridine and the mixture was stirred at room temperature for 63 hours. After concentration, the residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue was recrystallized from chloroform-ether to give 0.285 g of 2-(6-acetamido-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazin-4-yl)pyridine N-oxide.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-5625c65413ef4c4c8307c82a425e2200
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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