Water → 4-Bromo-3-[(dimethylamino)methyl]aniline

HRID 404571Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([Br:19])=[C:12]([CH:18]=1)[C:13]([N:15]([CH3:17])[CH3:16])=O.O.C(OCC)(=O)C>C1COCC1>[Br:19][C:11]1[CH:10]=[CH:9][C:8]([NH2:7])=[CH:18][C:12]=1[CH2:13][N:15]([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., LAH (1.5 g 40 mmol) was added slowly in several portions into a suspension of 5-amino-2-bromo-N,N-dimethylbenzamide (compound 26) (3.1 g, 12.7 mmol) in THF. The reaction mixture was stirred at 0° C. for 2 hours. Then at 0° C. water was added dropwise to the reaction solution slowly until there was no bubble forming in the reaction. After ethyl acetate was added, the reaction mixture was stirred for 30 minutes. The mixture was filtered, washed three times with ethyl acetate. The solvent was evaporated to give a crude product, which can be directly used for the next step.

Workup

customforming in the reaction
stirringthe reaction mixture was stirred for 30 minutes
filtrationThe mixture was filtered
washwashed three times with ethyl acetate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-7763394fb9314cf2ad69a20062477182
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748610B2

Reaction notes

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