Ammonium Chloride → HCID 71513092, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:18]([O-])=O)=[CH:5][C:6]([CH3:17])=[C:7]([C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH:8]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:18][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[O:10])=[C:6]([CH3:17])[CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To (5-methoxy-2-methyl-4-nitrophenyl)(morpholino)methanone (1.76 g, 6.3 mmol) in ethanol (25 mL) and water (25 mL) was added ammonium chloride (1.72 g, 31.5 mmol) and iron powder (1.41 g, 25.2 mmol). The mixture was heated to 90° C. for 2 hours and then filtered through celite, washed through with ethanol. The solvent was removed in vacuo and the residue was partitioned between water (50 mL) and DCM (50 mL). The layers were separated and the aqueous phase was washed with DCM (3×50 mL). The combined organic phases were dried over MgSO4, filtered and the solvent removed in vacuo. The residue was triturated with diethyl ether/40-60 petroleum ether and dried to give (4-amino-5-methoxy-2-methylphenyl)(morpholino)methanone (1.31 g, 82%) as an off-white solid.
Workup
- filtrationfiltered through celite
- washwashed through with ethanol
- customThe solvent was removed in vacuo
- customthe residue was partitioned between water (50 mL) and DCM (50 mL)
- customThe layers were separated
- washthe aqueous phase was washed with DCM (3×50 mL)
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- customthe solvent removed in vacuo
- customThe residue was triturated with diethyl ether/40-60 petroleum ether
- customdried
Sources & evidence
- ORD record
- ord-3a62dc4237354b2486da491dab8c5533
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809331B2
Reaction notes
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