3,4-Dihydro-6-methoxy-5-(phenylmethoxy)-2(1H)-isoquinolinecarboxaldehyde → HCID 21446991, compound

HRID 597206Notes

Reaction equation

HRID 597206 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([CH:21]=[O:22])[CH2:14]2)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH:21]([N:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:9]=2[OH:8])[CH2:14]1)=[O:22]

Participants

4

Reactant 1

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

Product 1

HCID 21446991HCID 21446991, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

89.2 g of 5-benzyloxy-2-formyl-1,2,3,4-tetrahydro-6-methoxy-isoquinoline are dissolved in 450 ml of glacial acetic acid and hydrogenated at room temperature and normal pressure in the presence of 4.5 g of 5 percent palladium black. After conclusion of hydrogen absorption, the reaction mixture is separated from the catalyst by filtration and evaporated to dryness under reduced pressure. Recrystallization of the residue from ethanol gives 57.2 g of 2-formyl-1,2,3,4-tetrahydro-5-hydroxy-6-methoxy-isoquinoline. m.p. = 172.5° - 173.5° C.

Workup

  1. customAfter conclusion of hydrogen absorption
  2. customthe reaction mixture is separated from the catalyst by filtration
  3. customevaporated to dryness under reduced pressure
  4. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-0840521759c84c31aff50d2e2ba013ab
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

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