4-(Dimethylamino)Benzaldehyde → HCID 54197884, compound

HRID 1703326Notes

Reaction equation

HRID 1703326 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[OH-].[Na+]>CO>[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH:11][C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][CH2:2][CH2:3]3)=[O:12])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium HydroxideHCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one

Product 1

HCID 54197884HCID 54197884, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.8 g of 1-(2,3-dihydro-1H-inden-5-yl)ethanone 5; 30 mmoles), 4.5 g of p-dimethylaminobenzaldehyde (30 mmoles), and 1.32 g of sodium hydroxide in 40 ml of methanol was stirred under nitrogen at room temperature for 48 hr. The reaction mixture was cooled in an ice bath and the precipitated solid 3-[4-(dimethylamino)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one was collected by filtration and washed with cold methanol. Yield: 4.2 g (48%); m.p. 106° to 108°. λmax (EtOH): 416 nm (ε=34,700); 272 nm (15,400). Calcd for C20H21NO: C, 82.44; H, 7.26; N, 4.81. Found: C, 82.19, 82.12; H, 7.21, 7.24; N, 4.70, 4.67.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitated solid 3-[4-(dimethylamino)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one was collected by filtration
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-4a608fc795ba4f239d39e54be846dedc
Source dataset
uspto-grants-1982_09
Patent number
US04351893

Reaction notes

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