2-Naphthalenecarboxaldehyde → HCID 67936478, compound

HRID 279976Notes

Reaction equation

HRID 279976 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[NH:13]([CH2:20][CH2:21][C:22]#[N:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>CS(C)=O.CO.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:21](=[CH:20][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:22]#[N:23]

Participants

7

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 141003-AnilinopropionitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 67936478HCID 67936478, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-naphthaldehyde (4.69 g, 30 mmol) and beta-anilinopropionitrile (4.82 g, 33 mmol) in dimethyl sulfoxide (35 ml) was added potassium t-butoxide (3.70 g, 33 mmol). The solution immediately turned a dark red. It was heated at 100° for 30 minutes, cooled, and diluted with methanol (15 ml) and water (25 ml). A copious yellow precipitate formed, which was chilled and isolated. The precipitate, 2-(2-naphthylmethyl)-3-anilinoacrylonitrile, was washed with dilute methanol and hexane; yield, 7.65 g. A portion was recrystallized from absolute ethanol; m.p. 148°-153° C. Anal. Calcd. for C20H16H2 : C, 84.48; H, 5.67; N, 9.85. Found: 84.38; H, 5.69; N, 9.82.

Workup

  1. temperatureIt was heated at 100° for 30 minutes
  2. temperaturecooled
  3. customA copious yellow precipitate formed
  4. temperaturewhich was chilled
  5. customisolated
  6. washThe precipitate, 2-(2-naphthylmethyl)-3-anilinoacrylonitrile, was washed with dilute methanol and hexane
  7. customyield
  8. customA portion was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-6149f9d4a3fb47fcaa30b4dde00fae6d
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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