Methoxyacetyl chloride → 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1041702Notes

Reaction equation

HRID 1041702 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:15][O:16][CH2:17][C:18](Cl)=[O:19]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:15][O:16][CH2:17][C:18]([N:8]1[C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:12][CH2:11][CH2:10][CH2:9]1)=[O:19]

Participants

5

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Product 1

HCID 672634692-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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) was treated with Methoxyacetyl chloride (0.15 mL, 1.6 mmol) was added to the vial and stirred at rt. After 4 h, the mixture was partitioned between EtOAc and water, separated and the org. layer was washed with 1N HCl. After washing with brine and drying, 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone was isolated following silica gel chromatography (0-100% EtOAc:Hex) as yellow solids (270 mg, 97%). 1H-NMR (CDCl3): 7.96 (m, 2H), 7.36 (m, 1H), 4.82 (m, 1H), 4.25 (m, 2H), 3.89 (m, 3H), 3.34 (s, 3H), 2.96 (m, 1H), 2.13 (m, 2H).

Workup

  1. additionwas added to the vial and
  2. customthe mixture was partitioned between EtOAc and water
  3. customseparated
  4. washlayer was washed with 1N HCl
  5. washAfter washing with brine
  6. customdrying

Sources & evidence

ORD record
ord-3b2a8b26d2fc4f1381b05c45a8e1fb79
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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