Hydrochloric Acid → HCID 73057458, compound

HRID 2207325Notes

Reaction equation

HRID 2207325 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][C:18](=[O:26])[C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][CH:11]=1.Cl>C1COCC1.CO>[OH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:17][C:18](=[O:26])[C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 73057150HCID 73057150, compound

Product 1

HCID 73057458HCID 73057458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, lithium aluminiumhydride (22.8 mg, 0.60 mmol) is added to a suspension of 4-(1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acid methyl ester (83.8 mg, 0.301 mmol) (for preparation see previous example) in THF (3 ml). The reaction mixture is stirred at ambient temperature for 16 hours. A few drops of methanol and then HCl (2 N aqueous solution, 0.5 ml) are added slowly to the reaction mixture. It is then filtered over a pad of celite. The filtrate is evaporated and the residue is triturated with tert-butyl methylether to afford 3-(4-hydroxymethyl-phenyl)-2H-isoquinolin-1-one as brown powder; HPLC/MS 1.55 min (A), [M+H] 252;

Workup

  1. filtrationIt is then filtered over a pad of celite
  2. customThe filtrate is evaporated
  3. customthe residue is triturated with tert-butyl methylether

Sources & evidence

ORD record
ord-edd70f5c3f504861b4416a33f80f2fe8
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

Loading…