Acetic Anhydride → HCID 67263601, compound

HRID 1041674Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[CH:21]=1)([O-:10])=[O:9].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C.CCOC(C)=O>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][N:16]([C:1](=[O:3])[CH3:2])[C:15]=2[CH:21]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

Acetic anhydride (1.00 mL, 10.6 mmol;) was added to a solution of 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.580 g, 2.99 mmol), 4-Dimethylaminopyridine (20 mg, 0.1 mmol; Acros) and Triethylamine (1.0 mL, 7.2 mmol) in Acetonitrile (10 mL; Acros). The reaction was stirred under an atmosphere of Nitrogen overnight. Conversion was moderate, so the mixture was heated at 50° C. for the weekend. The solution was conc. in vacuo, diluted with 25 mL EtOAc then washed with 1N HCl (10 mL), satd. sodium bicarbonate (10 mL) and brine (10 mL). After drying over sodium sulfate, the solution was conc. and the residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex) to afford 1-(2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone as light yellow solids (522 mg, 74%). Mixture of rotamers in 1H-NMR, resulting in very broad signals for the aliphatic methylenes. 13C-NMR (CDCl3): 169.8, 160.3, 142.7, 134.3, 124.8, 124.6, 122.6, 71.1, 45.0, 28.0, 22.4

Workup

washthen washed with 1N HCl (10 mL)
dry with materialAfter drying over sodium sulfate
customthe residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex)

Sources & evidence

ORD record: ord-9b59ed0e7e1849f49c41a5533e6d9008
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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