Pyridine → HCID 68123014, compound

HRID 597244Notes

Reaction equation

HRID 597244 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10](=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[NH:9][CH2:8][CH2:7]2.N1C=CC=CC=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>O>[CH:33]1([C:36]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:4]([O:3][CH3:2])[CH:5]=3)/[C:10]/2=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)=[O:37])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 681233903,4-Dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline hydrochloride

Product 1

HCID 68123014HCID 68123014, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 6 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline hydrochloride in 40 parts of pyridine is added 6 parts of cyclopropanecarbonyl chloride. The resultant mixture is stirred at room temperatures for 18 hours, then poured into 500 parts of water. The mixture thus obtained is extracted with chloroform. The chloroform extract is washed with 5% hydrochloric acid, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and dichloromethane to give (Z)-2-cyclopropylcarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline melting at 148°-151°.

Workup

  1. customThe mixture thus obtained
  2. extractionis extracted with chloroform
  3. extractionThe chloroform extract
  4. washis washed with 5% hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. customThe residue is crystallized from a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-7fc07fe7bd8a4cfb8f532fa703b4371d
Source dataset
uspto-grants-1977_03
Patent number
US04013666

Reaction notes

Loading…