Dichloromethane → HCID 71513092, compound

HRID 2406305Notes

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.O.O.Cl[Sn]Cl.[OH-].[Na+].C(Cl)Cl>C(O)C.O>[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]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To (5-methoxy-2-methyl-4-nitrophenyl)(morpholino)methanone (324 mg, 1.16 mmol) in ethanol (20 mL) and water (2 mL) was added SnCl2.2H2O (1.05 g, 4.64 mmol). The mixture was heated to 65° C. for 36 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-methylphenyl)(morpholino)methanone (268 mg, 92%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=251 at 2.14 min. 1H NMR (400 MHz, CDCl3): δ 6.60 (s, 1H), 6.52 (s, 1H), 3.87-3.52 (br m, 6H), 3.84 (br s, 2H), 3.82 (s, 3H), 3.36-3.23 (br m, 2H), 2.17 (s, 3H).

Workup

customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-b58e4541e86948e69df15227fc647640
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809331B2

Reaction notes

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