Hydrochloric Acid → HCID 10220820, compound

HRID 247392Notes

Reaction equation

HRID 247392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH3:19])[C:6]([CH:8]=[CH:9][C:10](O)=[O:11])=O.C(=O)([O-])[O-].[K+].[K+].Cl.O.[NH2:28][NH2:29]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[CH:8]=[CH:9][C:10](=[O:11])[NH:28][N:29]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 536961593-(3-Methoxy-4-n-propoxybenzoyl)acrylic acid

Product 1

HCID 10220820HCID 10220820, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.6 g of 3-(3-methoxy-4-n-propoxybenzoyl)acrylic acid and 6.1 g of potassium carbonate are dissolved in 100 ml of methanol and the solution is stirred overnight at room temperature. It is acidified with 7.4 ml of concentrated hydrochloric acid, 2.2 g of 100% pure hydrazine hydrate are added to the mixture and the mixture is boiled under reflux for 3 hours. It is then acidified to pH 1 with 1 ml of hydrochloric acid and 75 ml of methanol are distilled off in the course of 2 hours. The mixture is allowed to cool and the crystal mass is filtered off with suction, suspended several times in 50 ml of water each time, filtered off with suction and, finally, dried in vacuo. 6.6 g (63.7% of theory) of the title compound of m.p. 169°-171° are obtained. After recrystallization from ethanol/ethyl acetate, the m.p. rises to 172°.

Workup

  1. additionare added to the mixture
  2. temperatureunder reflux for 3 hours
  3. distillationare distilled off in the course of 2 hours
  4. temperatureto cool
  5. filtrationthe crystal mass is filtered off with suction
  6. filtrationfiltered off with suction
  7. customfinally, dried in vacuo

Sources & evidence

ORD record
ord-7fc107acb2234352a3ed5008d2ae1861
Source dataset
uspto-grants-1987_11
Patent number
US04707481

Reaction notes

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