Hydrochloric Acid → HCID 178511051, compound

HRID 1417321Notes

Reaction equation

HRID 1417321 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:9][CH:8]=1)=O.[NH2:30]N.Cl>C(O)C>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:9][CH:8]=2)=[N:30]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 67693872(E)-2-[4-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 178511051HCID 178511051, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 21.2 g of (E)-2-[4-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenoxy]butyl]-1H-isoindole-1,3(2H)-dione (Example 48) in 300 ml of boiling ethanol is treated with 6 ml of anhydrous hydrazine. A suspension quickly develops, necessitating addition of 200 ml more ethanol to permit stirring. While stirring 35 ml of concentrated HCl is then added, the mixture refluxed a further hour, and filtered hot. The insolubles are washed with 200 ml of boiling water. The combined filtrates are taken to dryness in vacuo, leaving the hydrochloride salt of the title compound as shown by mass spectrometry. The product is utilized for synthesis without further purification.

Workup

  1. additionis then added
  2. temperaturethe mixture refluxed a further hour
  3. filtrationfiltered hot
  4. washThe insolubles are washed with 200 ml of boiling water

Sources & evidence

ORD record
ord-08b8c687defc4f8992f3b72deabcfd69
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

Loading…