Dichloromethane → (4-Amino-5-chloro-2-methylphenyl)(morpholino)methanone

HRID 2406310Notes

Reaction equation

HRID 2406310 reaction equation
[Cl:1][C:2]1[C:3]([N+:17]([O-])=O)=[CH:4][C:5]([CH3:16])=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[CH:7]=1.O.O.Cl[Sn]Cl.[OH-].[Na+].C(Cl)Cl>C(O)C.O>[NH2:17][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[C:5]([CH3:16])[CH:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 71512863HCID 71512863, compound

Product 1

HCID 71513091(4-Amino-5-chloro-2-methylphenyl)(morpholino)methanoneYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To (5-chloro-2-methyl-4-nitrophenyl)(morpholino)methanone (244 mg, 0.86 mmol) in ethanol (6 mL) and water (0.6 mL) was added SnCl2.2H2O (776 mg, 3.44 mmol). The mixture was heated to 65° C. for 5 h and then 2 M aqueous sodium hydroxide solution (10 mL) and DCM (10 mL) were added. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give (4-amino-5-chloro-2-methylphenyl)(morpholino)methanone (203 mg, 93%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=255 at 2.84 min. 1H NMR (400 MHz, CDCl3): δ 7.07 (s, 1H), 6.60 (s, 1H), 4.10 (br s, 2H), 3.84-3.53 (br m, 6H), 3.36-3.24 (br m, 2H), 2.21 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-22be813b68f3411e8c604404cc5fffde
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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