4-(Dimethylamino)Benzaldehyde → HCID 15219578, compound

HRID 1416338Notes

Reaction equation

HRID 1416338 reaction equation
[CH3:1][N:2]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:3].[I-].[CH3:13][C:14]1[CH:19]=[CH:18][N+:17]([CH3:20])=[CH:16][CH:15]=1.[C:21]1([B-:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+]>>[C:40]1([B-:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1.[CH3:1][N:2]([C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:13]/[C:14]2[CH:19]=[CH:18][N+:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)[CH3:3]

Participants

4

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 2006031,4-Dimethylpyridin-1-ium iodideHCID 2723787Sodium Tetraphenylborate

Product 1

HCID 15219578HCID 15219578, compoundYield 70%

Procedure

14.9 g (0.1 mol) of 4-(N,N-dimethylamino)benzaldehyde were reacted with 23.6 g (0.1 mol) of 4-methyl-N-methylpyridinium iodide, prepared according to Example 3, and the resulting solution was treated with 34.6 g (0.1 mol) of sodium tetraphenyborate, under the conditions described in Example 6, to form dye2 as a red solid in a yield of 70%. 1H-NMR (DMSO-d6) δ3.00 (s, 6H), 4.1 (s, 3H), 6.70 (t, 4H), 6.8 (t, d, 2H), 6.9 (t, 8H), 7.02 (d, 1H), 7.10 (d, 8H) 7.50 d, 2H), 7.9 (d, 1H), 8.0 (d, 2H), 8.62 (d, 2H) ppm. Td 266° C.

Workup

  1. customprepared
  2. customto form dye2 as a red solid in a yield of 70%
  3. customTd 266° C.

Sources & evidence

ORD record
ord-632d1ffc6aa34e58a9be3b4b68c0a9b4
Source dataset
uspto-grants-1999_06
Patent number
US05912257

Reaction notes

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