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

HRID 1512167
Notes
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Reaction equation

HRID 1512167 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 67528873HCID 67528873, compound

Product 1

HCID 67527695(E)-N-(3-amino-2'-trifluoromethyl-biphenyl-4-yl)-3-(tetrahydro-pyran-4-yl)-acrylamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst
HCID 887
Methanol
Solvent
HCID 962WaterSolvent

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

  1. extractionextracted with EtOAc (2×30 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes