Stannous Chloride → 7-Amino-6-methoxy-2,2,4-trimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2401480Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

6-Methoxy-2,2,4-trimethyl-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (250 mg, 0.94 mmol) was stirred in ethanol (15 mL) then tin (II) chloride was added. The reaction was heated to 80° C. with stirring for 2 h. The volatiles were removed under reduced pressure and the residue was slurried with 2M sodium hydroxide aqueous solution. The aqueous was extracted with ethyl acetate and the combined organic extracts were passed through a phase separation cartridge and evaporated, to afford a brown crystalline solid (220 mg, 99%) which was taken through to the next step with no further purification.

Workup

customThe volatiles were removed under reduced pressure
extractionThe aqueous was extracted with ethyl acetate
customthe combined organic extracts were passed through a phase separation cartridge
customevaporated

Sources & evidence

ORD record: ord-d6881cacb0af447fb28bdcca83c9e48c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796296B2

Reaction notes

Loading…