Ammonium Chloride → (E)-N-(3-amino-2'-trifluoromethyl-biphenyl-4-yl)-3-(tetrahydro-pyran-4-yl)-acrylamide

HRID 1512167Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH:7]=[CH:8][C:9]=1[NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)([O-])=O.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>CO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:28])[F:29])[CH:7]=[CH:8][C:9]=1[NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[CH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (E)-N-(3-nitro-2′-trifluoromethyl-biphenyl-4-yl)-3-(tetrahydro-pyran-4-yl)-acrylamide (82.0 mg, 0.195 mmol) in MeOH (5 mL) and water (5 mL) was treated with NH4Cl (104 mg, 1.95 mmol) and Fe powder (54.5 mg, 0.975 mmol) and heated to 50° C. for 1 h. The cooled mixture was treated with saturated aqueous NaHCO3 (30 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to yield (E)-N-(3-amino-2′-trifluoromethyl-biphenyl-4-yl)-3-(tetrahydro-pyran-4-yl)-acrylamide as a colorless glassy solid.

Workup

extractionextracted with EtOAc (2×30 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7405234268964ebba2bcf4b2b1c61be1
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217060B2

Reaction notes

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