Sodium borohydride → 2-[2-Ethoxy-5-(1-hydroxy-2-morpholinoethyl)phenyl]-8-methylquinazolin-4(3H)-one

HRID 412023Notes

Reaction equation

HRID 412023 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][C:5]=1[C:19]1[NH:28][C:27](=[O:29])[C:26]2[C:21](=[C:22]([CH3:30])[CH:23]=[CH:24][CH:25]=2)[N:20]=1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:18])[CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][C:5]=1[C:19]1[NH:28][C:27](=[O:29])[C:26]2[C:21](=[C:22]([CH3:30])[CH:23]=[CH:24][CH:25]=2)[N:20]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 135714917HCID 135714917, compound

Product 1

HCID 1357149092-[2-Ethoxy-5-(1-hydroxy-2-morpholinoethyl)phenyl]-8-methylquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Ethoxy-5-morpholinoacetylphenyl)-8-methylquinazolin-4(3H)-one (Example 16; 0.2 g, 0.00049 mol) was suspended in stirred ethanol (30 ml) and the mixture treated with sodium borohydride (0.0018 g, 0.00049 mol). After 18 hours at room temperature, the solvent was evaporated under vacuum. The residue was suspended in saturated aqueous sodium carbonate solution (30 ml) and the suspension extracted with ethyl acetate (3×20 ml). The extracts were combined, dried (Na2SO4) and evaporated under vacuum, then the residue crystallized from ethyl acetate-hexane to give the title compound as colorless plates (0.14 g, 70%), m.p. 145-147° C.

Workup

  1. customthe solvent was evaporated under vacuum
  2. extractionthe suspension extracted with ethyl acetate (3×20 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customthe residue crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2413ebfa70f14fcfaf218062137688f2
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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