2,4,4-trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one → 8-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

HRID 633457Notes

Reaction equation

HRID 633457 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[N:5]2[C:6]3[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:7]=3[O:8][C:9]([CH3:11])([CH3:10])[C:4]2=[N:3]1>CO.[Pd]>[NH2:16][C:14]1[CH:13]=[CH:12][C:7]2[O:8][C:9]([CH3:11])([CH3:10])[C:4]3[N:5]([C:19](=[O:20])[N:2]([CH3:1])[N:3]=3)[C:6]=2[CH:15]=1

Participants

4

Reactant 1

HCID 867045432,4,4-trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

Product 1

HCID 867045448-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-oneYield 110.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,4,4-Trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (249 mg) and 10% Pd—C were suspended in methanol (5 mL). The reaction mixture was stirred at room temperature under H2 atmosphere (1 atm) overnight. The catalyst was filtered off over celite and washed with methanol (5×20 mL). The filtrate was evaporated to give 8-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (245 mg, quant).

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. washwashed with methanol (5×20 mL)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d901a16435ab443bbf96d5d141376198
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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