4-(Dimethylamino)Benzaldehyde → n-(5-Carboxypentyl)-4-(4-(dimethylamino)styryl)pyridinium bromide

HRID 1717432Notes

Reaction equation

[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1)[CH3:3].[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1C)([OH:15])=[O:14].N1CCCC[CH2:29]1>C(O)C>[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:22]=[CH:23][C:24]([CH:29]=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([N:2]([CH3:1])[CH3:3])=[CH:9][CH:8]=2)=[CH:25][CH:26]=1)([OH:15])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-N,N-dimethylaminobenzaldehyde (3 g, 20 mmoles), N-(5-carboxypentyl)picolinium bromide (5.6 g, 20 mmoles) and piperidine (2 mL) in ethanol (100 mL) was heated at 60° C. overnight. The mixture was evaporated to dryness in vacuo. The residue was redissolved in methanol and then precipitated with ether to give the title product (6.7 g).

Workup

customThe mixture was evaporated to dryness in vacuo
dissolutionThe residue was redissolved in methanol
customprecipitated with ether

Sources & evidence

ORD record: ord-3d5a6cb7c6424835a449852a6cfd6285
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803943B2

Reaction notes

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