Sodium Hydroxide → 1-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

HRID 1295998Notes

Reaction equation

[OH-].[Na+].C([N:6]1[C:11]2[CH:12]=[C:13]([C:20](=[O:22])[CH3:21])[CH:14]=[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=2[O:9][CH2:8][CH2:7]1)(=O)C>CO>[C:16]([C:15]1[C:10]2[O:9][CH2:8][CH2:7][NH:6][C:11]=2[CH:12]=[C:13]([C:20](=[O:22])[CH3:21])[CH:14]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

After adding 6 N aqueous sodium hydroxide (180 ml, 900 mmol) to a solution of the 1-[4-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone (36.8 g, 134 mmol) in methanol (360 ml) under a nitrogen atmosphere, the mixture was stirred at 70° C. for 40 minutes. The methanol was distilled off under reduced pressure, and the precipitated crystals were filtered out and dried under reduced pressure to yield the title compound (30.6 g, 98.1% yield) as bright golden yellow crystals.

Workup

distillationThe methanol was distilled off under reduced pressure
filtrationthe precipitated crystals were filtered out
customdried under reduced pressure

Sources & evidence

ORD record: ord-a1994b38a0ae46abab09b03c403154e4
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244730B2

Reaction notes

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