Hydrochloric Acid → HCID 68142865, compound

HRID 1579310Notes

Reaction equation

HRID 1579310 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:9][O:10][C:11](=[O:33])[C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH2:20][C:21]([C:29]#N)=[CH:22][N:23]2CCOCC2)=[CH:14][C:13]=1[O:31][CH3:32]>C(O)(C)C>[CH3:9][O:10][C:11](=[O:33])[C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH2:20][C:21]([C:22]#[N:23])=[CH:29][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 53975458HCID 53975458, compound

Product 1

HCID 68142865HCID 68142865, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8.6 G. of aniline were treated under cooling with 7.6 ml. of concentrated hydrochloric acid. Subsequently, 32 g. of 4-(2-cyano-3-morpholinoallyl)-2,6-dimethoxybenzoic acid methyl ester and 100 ml. of isopropanol were added. The suspension was heated at reflux with stirring for 30 minutes. About 1/3 to half of the solvent was evaporated and 20 ml. of water added. The resulting crystalline product was removed by filtration under vacuum, washed with a little cold methanol and dried. Recrystallization from methanol yielded 4-(3-anilino-2-cyanoallyl)-2,6-dimethoxybenzoic acid methyl ester of m.p. 193°-194°.

Workup

  1. temperatureunder cooling with 7.6 ml
  2. temperatureThe suspension was heated
  3. temperatureat reflux
  4. customAbout 1/3 to half of the solvent was evaporated
  5. additionof water added
  6. customThe resulting crystalline product was removed by filtration under vacuum
  7. washwashed with a little cold methanol
  8. customdried
  9. customRecrystallization from methanol

Sources & evidence

ORD record
ord-ddeaa1cedfd049f4a2e186d97bb67b03
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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