3'-Nitro-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester → 3'-Amino-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester

HRID 1069081Notes

Reaction equation

HRID 1069081 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:4]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:4]

Participants

4

Reactant 1

HCID 544941873'-Nitro-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester

Product 1

HCID 541671593'-Amino-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

n.m.r. (DMSO-d6) δ values include 3.77 (s, 2 H), 3.91 (s, 3 H), 3.92 (s, 3 H), 6.70 (m, 1 H), 6.89 (s, 1 H), 6.97 (d, 1 H), 7.21 (d, 1 H), 7.69 (m, 1 H), 7.79 (d, 1 H), 7.85 (m, 1 H); from 3′-nitro-[1,1′-biphenyl]-3,4-dicarboxylic acid dimethyl ester (0.8 g) and 10% Pd/C (560 mg) in tetrahydrofuran (30 mL).

Sources & evidence

ORD record
ord-95ee9564c8614bb891cbada6d74db3da
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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