HCID 21034909, compound → HCID 22048353, compound

HRID 1833112Notes

Reaction equation

HRID 1833112 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[N:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[C:6]([CH2:4][OH:3])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 21034909HCID 21034909, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22048353HCID 22048353, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above 1-(3-methoxybenzyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid ethyl ester (1.50 g, 3.94 mmol) was dissolved into 30 ml of THF. To this solution was added lithium aluminum hydride (240 mg, 6.49 mmol). The mixture was refluxed for 30 minutes and then poured into ice and extracted with methylene chloride and saturated ammonium chloride solution. The organic layer was dried with sodium sulfate and solvents were evaporated. The residue was washed with ether to give a white solid 1-(3-methoxybenzyl)-4-hydroxymethyl-6,7-dimethoxyisoquinoline (1.13 g, 85%). ES-MS calculated for C20H21O4N (m/e) 339.39, observed 340.5 (M+1). 1H-NMR is consistent with the desired structure.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. additionpoured into ice
  3. extractionextracted with methylene chloride and saturated ammonium chloride solution
  4. dry with materialThe organic layer was dried with sodium sulfate and solvents
  5. customwere evaporated
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-fbd02af7701e4d43a162d016b0436594
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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