Methyl 4-aminobenzoate → Methyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate

HRID 1290598Notes

Reaction equation

HRID 1290598 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]12([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH:25]=O)[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>ClCCl>[C:12]12([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH:25]=[N:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=3)[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]3)[CH2:19]1)[CH2:21]2

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde

Product 1

HCID 67591566Methyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g of basic alumina and 1.94 g (12.9 mmoles) of methyl 4-aminobenzoate are mixed in a mortar, then introduced into a round bottom flask. 3 g (11.1 mmoles) of 3-(1-adamantyl)-4-methoxybenzaldehyde in 50 ml of anhydrous dichloromethane are added with stirring. After heating at reflux for 24 hours, the reaction medium is extracted with dichloromethane and evaporated to dryness. The crude product is recrystallized in a mixture of ethyl acetate and acetone. After filtration, 3.4 g (75%) of the expected product whose melting point is 180°-182° C. are obtained.

Workup

  1. additionintroduced into a round bottom flask
  2. temperatureAfter heating
  3. temperatureat reflux for 24 hours
  4. extractionthe reaction medium is extracted with dichloromethane
  5. customevaporated to dryness
  6. customThe crude product is recrystallized in a mixture of ethyl acetate and acetone
  7. filtrationAfter filtration, 3.4 g (75%) of the expected product whose melting point is 180°-182° C.
  8. customare obtained

Sources & evidence

ORD record
ord-d9577ea974d04a0585e3319f112d4521
Source dataset
uspto-grants-1998_05
Patent number
US05753239

Reaction notes

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