Stannous Chloride → 3'-Amino-4-fluorobiphenyl-2-carbonitrile

HRID 478254Notes

Reaction equation

HRID 478254 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17]#[N:18])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:6][CH:7]=1.[Sn](Cl)Cl>C(O)C.O1CCCC1>[NH2:14][C:10]1[CH:9]=[C:8]([C:5]2[C:4]([C:17]#[N:18])=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 222853434-Fluoro-3'-nitrobiphenyl-2-carbonitrile

Product 1

HCID 222852793'-Amino-4-fluorobiphenyl-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoro-3′-nitrobiphenyl-2-carbonitrile was reduced by treatment with tin(II) chloride in ethanol and tetrahydrofuran to give 3′-amino-4-fluorobiphenyl-2-carbonitrile as a brown solid: δH (360 MHz, CDCl3) 6.76 (1H, ddd, J 8, 2 and 2), 6.80 (1H, dd, J 2 and 2), 6.87 (1H, ddd, J 8, 1 and 1), 7.27 (1H, dd, J 8 and 8), 7.35 (1H, ddd, J 8, 8 and 3), 7.41-7.51 (2H, m).

Sources & evidence

ORD record
ord-100098b16d204799af3ad5180ed7b283
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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