Ammonium Chloride → Morpholine, 4-[3-amino-5-(trifluoromethyl)benzoyl]-

HRID 1446699Notes

Reaction equation

HRID 1446699 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>CO.[Zn]>[NH2:19][C:11]1[CH:10]=[C:9]([C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[O:8])[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 219549894-(3-Nitro-5-trifluoromethyl-benzoyl)-morpholine

Product 1

HCID 66876746Morpholine, 4-[3-amino-5-(trifluoromethyl)benzoyl]-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Dissolve the morpholin-4-yl-(3-nitro-5-trifluoromethyl-phenyl)-methanone (830 mg, 2.7 mmol) in MeOH (40 mL) at room temperature. Add ammonium chloride (3 g, 56 mmol) and stir at for 10 minutes before adding Zn powder (5 g, 76 mmol) with stirring for another 5-10 minutes. Filter and wash with MeOH. Concentrate to a white solid of 2 g material, containing excess ammonium chloride. LCMS (ES), m/z 275 (M+1). Use in the next step without further purification.

Workup

  1. filtrationFilter
  2. washwash with MeOH
  3. concentrationConcentrate to a white solid of 2 g material
  4. additioncontaining excess ammonium chloride
  5. customUse in the next step without further purification

Sources & evidence

ORD record
ord-558cef6793474ae7bfd86396cd841c96
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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