4-(Dimethylamino)Benzaldehyde → HCID 54256011, compound

HRID 1703328Notes

Reaction equation

HRID 1703328 reaction equation
[C:1]1(=[O:14])[C:9]2[CH:8]=[C:7]3[CH2:10][CH2:11][CH2:12][CH2:13][C:6]3=[CH:5][C:4]=2[CH2:3][CH2:2]1.[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.[OH-].[Na+]>C(O)C>[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:2]2[C:1](=[O:14])[C:9]3[CH:8]=[C:7]4[CH2:10][CH2:11][CH2:12][CH2:13][C:6]4=[CH:5][C:4]=3[CH2:3]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium HydroxideHCID 10583718HCID 10583718, compound

Product 1

HCID 54256011HCID 54256011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.84 g (10 mmoles) of 2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one (12), 1.49 g (10 mmoles) of p-dimethylaminobenzaldehyde, and 0.44 g of sodium hydroxide in 25 ml ethanol was stirred under nitrogen at 50° to 60° for 19 hr. The reaction mixture was cooled in an ice bath and the precipitated solid 2-[4-(dimethylamino)phenyl)-methylene]-2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one was collected by filtration and washed with cold ethanol. Yield: 2.5 g (79%); m.p. 161° to 163°. λmax (EtOH): 274 nm (ε=16,700); 422 nm (36,500). Calcd for C22H23NO: C, 83.24; H, 7.30; N, 4.41. Found: C, 83.01; H, 7.73; N, 4.34.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitated solid 2-[4-(dimethylamino)phenyl)-methylene]-2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one was collected by filtration
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-d7dfbacfd51e432abf04ea10e7b7f2c2
Source dataset
uspto-grants-1982_09
Patent number
US04351893

Reaction notes

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