(4-Methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl ester → HCID 23593643, compound

HRID 1611961Notes

Reaction equation

HRID 1611961 reaction equation
[CH3:1][O:2][C:3](=[O:19])[NH:4][C:5]1[O:6][C:7]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[C:8]=2[N:9]=1>CO.ClCCl.[Pd]>[CH3:1][O:2][C:3](=[O:19])[NH:4][C:5]1[O:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[C:8]=2[N:9]=1

Participants

5

Reactant 1

HCID 23593644(4-Methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 23593643HCID 23593643, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 220 mg (0.82 mmol) (4-methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl ester in 25 ml methanol and 45 ml dichloromethane was added a spatula end of 10% palladium on charcoal and stirring continued for 18 h at room temperature under an atmosphere of hydrogen. The mixture was then filtered and the filtrate concentrated in vacuo. Flash chromatography (2/98 methanol/dichloromethane) afforded 114 mg (58%) (7-amino-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester as a white crystalline solid. ES-MS m/e (%): 238 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2bf98742e4d94c55b3a352f6a662c1e0
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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