2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one → 6-amino-2,2,4-trimethyl-2H-1,4-benzoxazine-3(4H)-one

HRID 633469Notes

Reaction equation

HRID 633469 reaction equation
[CH3:1][C:2]1([CH3:17])[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:4]=2[O:3]1>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:4]2[O:3][C:2]([CH3:1])([CH3:17])[C:7](=[O:8])[N:6]([CH3:9])[C:5]=2[CH:10]=1

Participants

4

Reactant 1

HCID 136655432,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 136655826-amino-2,2,4-trimethyl-2H-1,4-benzoxazine-3(4H)-oneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (290 mg, 1.23 mmol, 1 equiv.) in 10 mL of MeOH in the presence of 29 mg of Pd/C was hydrogenated at room temperature for 3 h. The reaction mixture was then filtered through a pad of celite and the filtrate was concentrated to give 240 mg (Yield=95%) of product as a pale brown solid which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d280986bc450498589d9beefe09e5342
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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