Acetyl chloride → 1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1688040Notes

Reaction equation

HRID 1688040 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[N+:5]([C:8]1[CH:18]=[CH:17][C:11]2[NH:12][CH2:13][CH2:14][CH2:15][O:16][C:10]=2[CH:9]=1)([O-:7])=[O:6]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N+:5]([C:8]1[CH:18]=[CH:17][C:11]2[N:12]([C:1](=[O:3])[CH3:2])[CH2:13][CH2:14][CH2:15][O:16][C:10]=2[CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Product 1

HCID 672644451-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanoneYield 91.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.080 mL, 1.1 mmol) was added to 3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (203 mg, 1.04 mmol) and 4-Dimethylaminopyridine (13 mg, 0.10 mmol) in Pyridine (3.5 mL) and the reaction was stirred at room temperature overnight. The mixture was partitioned between 20 mL EtOAc and 20 mL satd. sodium bicarbonate, the org. was then washed with 1N HCl (20 mL) and brine (20 mL), dried and conc. in vacuo to give 1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone as yellow solids (225 mg, 91%).

Workup

  1. customThe mixture was partitioned between 20 mL EtOAc and 20 mL
  2. washwas then washed with 1N HCl (20 mL) and brine (20 mL)
  3. customdried and conc. in vacuo

Sources & evidence

ORD record
ord-ee23eb6a329345c29a82600cd74133b1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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