N-(5,5-Dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2-methoxy-acetamide → (5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-(2-methoxy-ethyl)-amine

HRID 1687670Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][C:5](=O)[CH:4]([NH:17][C:18](=O)[CH2:19][O:20][CH3:21])[CH2:3]1>C1COCC1>[CH3:1][C:2]1([CH3:23])[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][CH2:5][CH:4]([NH:17][CH2:18][CH2:19][O:20][CH3:21])[CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of N-(5,5-Dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2-methoxy-acetamide (0.138 g, 0.43 mmol) in THF (10 mL, 0.1 mol) was treated with 1 M of Borane-THF complex in THF (3 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was quenched by the slow dropwise addition of methanol until all bubbling ceased, was concentrated, taken up in CH2Cl2 and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure.

Workup

customThe reaction mixture was quenched by the slow dropwise addition of methanol until all bubbling
concentrationwas concentrated
washwashed with water
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a1bb30abe8f14ac18e771b09753e12d0
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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