Hydrochloric Acid → 3-Hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline

HRID 1084440Notes

Reaction equation

HRID 1084440 reaction equation
[CH3:1][N:2]1[C:11]([C:12](Cl)=[O:13])=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21].[BH4-].[Na+].Cl.O>O1CCCC1.C(OCC)C>[OH:13][CH2:12][C:11]1[N:2]([CH3:1])[C:3](=[O:21])[C:4]2[C:9]([C:10]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydride2×HCID 126891202-Methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

Product 1

HCID 152141953-Hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride (5.96 g; prepared according to the method of F. Duro et al., Il. Farmaco Ed. Sci., 36,400) in dry tetrahydrofuran (120 ml) was treated, portionwise, with sodium borohydride (1.68 g) and the mixture was stirred at room temperature for 4 hours. A further portion of sodium borohydride (0.4 g) was then added and the mixture was stirred for a further period of 30 minutes. The reaction mixture was then treated, dropwise, with dilute hydrochloric acid (60 ml; 2N) and then with water (80 ml). The mixture was diluted with diethyl ether (200 ml) and the organic phase was separated, washed with water (2×80 ml), dried over magnesium sulphate and evaporated. The resulting residue was crystallised from ethyl acetate, to give 3-hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline (3.5 g) in the form of white crystals, m.p.159°-161° C. [Elemental analysis: C,77.2; H,5.76; N,5.37%; calculated: C,77.0; H,5.70; N,5.28%].

Workup

  1. customprepared
  2. additionThe reaction mixture was then treated
  3. customthe organic phase was separated
  4. washwashed with water (2×80 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe resulting residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-b3fd3cc415ad4b4688f9d47cddfa58c1
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

Loading…