Potassium Hydroxide → 2,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

HRID 1688008Notes

Reaction equation

HRID 1688008 reaction equation
[OH-].[K+].C(OC([N:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1)=O)C>O.COCCO>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]2[O:12][CH2:11][CH2:10][CH2:9][NH:8][C:14]=2[CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 672634892-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester

Product 1

HCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepineYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

1.00 M of Potassium hydroxide in Water (25 mL) was added to 2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester (2.84 g, 10.7 mmol) in 2-Methoxyethanol (50 mL) and the reaction was heated at 110° C. After overnight heating, the mixture was cooled, extracted with DCM (2×50 mL); the combined organics were washed with water (50 mL) and brine (50 mL), dried and conc. in vacuo. The residue was chromatographed (120 g SiO2, ISCO, 0-20% EtOAc:Hex) to afford 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as an orange solid (1.64 g, 79%).

Workup

  1. temperatureAfter overnight heating
  2. temperaturethe mixture was cooled
  3. extractionextracted with DCM (2×50 mL)
  4. washthe combined organics were washed with water (50 mL) and brine (50 mL)
  5. customdried and conc. in vacuo
  6. customThe residue was chromatographed (120 g SiO2, ISCO, 0-20% EtOAc:Hex)

Sources & evidence

ORD record
ord-aedeba6a4103494dad23d751187fb3ce
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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