Dichloromethane → (4-Amino-5-methoxy-2-(trifluoromethyl)phenyl)(morpholino)methanone

HRID 2406312Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([N+:21]([O-])=O)=[CH:5][C:6]([C:17]([F:20])([F:19])[F:18])=[C:7]([C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH:8]=1.O.O.Cl[Sn]Cl.[OH-].[Na+].C(Cl)Cl>C(O)C.O>[NH2:21][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]([C:17]([F:20])([F:19])[F:18])[CH:5]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To (5-methoxy-4-nitro-2-(trifluoromethyl)phenyl)(morpholino)methanone (349 mg, 1.04 mmol) in ethanol (20 mL) and water (2 mL) was added SnCl2.2H2O (941 mg, 4.16 mmol). The mixture was heated to 65° C. for 2 h and then 2 M aqueous sodium hydroxide solution (20 mL) and DCM (20 mL) were added. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo to give (4-amino-5-methoxy-2-(trifluoromethyl)phenyl)(morpholino)methanone (250 mg, 79%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=305 at 2.87 min. 1H NMR (400 MHz, CDCl3): δ 6.94 (s, 1H), 6.64 (s, 1H), 4.07 (s, 2H), 3.92-3.67 (m, 4H), 3.89 (s, 3H), 3.62-3.52 (m, 2H), 3.25-3.19 (m, 2H).

Workup

customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-990e7506033d4263a9431717d81d5a8d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809331B2

Reaction notes

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