Formamide → 3,4-Dihydro-6-methoxy-5-(phenylmethoxy)-2(1H)-isoquinolinecarboxaldehyde

HRID 597205Notes

Reaction equation

HRID 597205 reaction equation
Cl.[CH2:2]([O:9][C:10]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][NH:14][CH2:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:22](N)=[O:23]>C(O)=O>[CH2:2]([O:9][C:10]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][N:14]([CH:22]=[O:23])[CH2:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 21447025HCID 21447025, compound

Product 1

HCID 214470373,4-Dihydro-6-methoxy-5-(phenylmethoxy)-2(1H)-isoquinolinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

122.3 g of 5-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-isoquinoline-hydrochloride, 140 ml of formic acid, and 700 ml of formamide are heated for 2.5 hours under reflux. The mixture is then poured over 2 kg of ice and extracted with methylene chloride. After evaporation to dryness of the methylene chloride solution under reduced pressure, the residue is recrystallized from methanol-water. 102.3 g of 5-benzyloxy-2-formyl-1,2,3,4-tetrahydro-6-methoxy-isoquinoline are obtained. m.p. = 117.5° - 118.5° C.

Workup

  1. temperatureunder reflux
  2. extractionextracted with methylene chloride
  3. customAfter evaporation to dryness of the methylene chloride solution under reduced pressure
  4. customthe residue is recrystallized from methanol-water

Sources & evidence

ORD record
ord-19e1809fd83448d585d95d53f826d49e
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

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