Methyl 3-(3,4-dinitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate → Methyl 3-(3,4-diaminobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

HRID 655318Notes

Reaction equation

HRID 655318 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[CH2:7][N:8]1[C:12]2[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]1=[O:21])([O-])=O>C1COCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:24]=1[NH2:25])[CH2:7][N:8]1[C:12]2[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]1=[O:21]

Participants

4

Reactant 1

HCID 58486041Methyl 3-(3,4-dinitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

Product 1

HCID 58486039Methyl 3-(3,4-diaminobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.45 g (3.8 mmol) of methyl 3-(3,4-dinitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate are dissolved in 20 ml of THF and hydrogenated under a hydrogen atmosphere using 1 g of Raney nickel (water-wet). After 24 h, the reaction solution is filtered, and the filtrate is evaporated to dryness; product: 1.1 g, ESI: 314 (M+H).

Workup

  1. filtrationthe reaction solution is filtered
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-db2b338e12b64ba198ab9d98979a4d81
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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