Ammonia → 3-Amino-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

HRID 922390Notes

Reaction equation

HRID 922390 reaction equation
F[C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]#[N:9].[NH3:18]>>[NH2:18][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 867193543-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 867193553-Amino-5-methoxy-[1,1'-biphenyl]-4-carbonitrileYield 52%

Procedure

A solution of 3-fluoro-5-methoxy-[1,1′-biphenyl]-4-carbonitrile (3, 4.0 g, 17.6 mmol) in ammonia saturated DMSO (100 mL) was heated in an autoclave at 150° C. for 18 h. After this time, the mixture was cooled to room temperature, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (2.06 g, 52%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ7.54-7.52 (m, 2H), 7.46-7.43 (m, 2H), 7.41-7.38 (m, 1H), 6.52 (d, J=1.0 Hz, 1H), 6.43 (d, J=1.0 Hz, 1H), 4.43 (br s, 2H), 3.93 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography
  3. washeluting with ethyl acetate in hexane (0-100%)

Sources & evidence

ORD record
ord-c11e64d9a3be43bf85d4f43ac22777a8
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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