(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester → N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

HRID 717525Notes

Reaction equation

HRID 717525 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-])=O)[CH:3]=1>[Zn]>[NH2:16][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14]

Participants

3

Reactant 1

HCID 59705030(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

The title compound was prepared from the tert-butyl 4-fluoro-2-nitrophenylcarbamate (Example A6; 3 mmol) by reduction with zinc according to the general procedure B. Obtained as a yellow solid (66%), MS (EI) 227 [(M+1)+].

Sources & evidence

ORD record
ord-15297f284e624d0188838d8b07deadb7
Source dataset
uspto-grants-2015_11
Patent number
US09193710B2

Reaction notes

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