Methanol → HCID 19816066, compound

HRID 2247895Notes

Reaction equation

HRID 2247895 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[NH:14][CH2:13]3)=[O:9])[CH:3]=1.CO.[OH-].[Na+].[BH4-].[Na+]>O.C(O)(=O)C>[OH:9][CH:8]([C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[NH:14][CH2:13]2

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 19816050HCID 19816050, compound

Product 1

HCID 19816066HCID 19816066, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 4.35 parts of intermediate 2, namely 3,4-dihydro-6-(3-pyridinylcarbonyl)-2(1H)-quinazolinone monohydrochloride, 63.2 parts of methanol, 1.2 parts of sodium hydroxide and 15 parts of water were added portionwise 0.6 parts of sodium tetrahydroborate. After stirring for 2 hours at room temperature, there was added a mixture of 2.1 parts of acetic acid in 25 parts of water. The precipitate was filtered off, washed with water, 2-propanol and 1,1'-oxybisethane and dried, yielding 3.7 parts (96.6%) of 3,4-dihydro-6-[hydroxy(3-pyridinyl)methyl]-2(1H)-quinazolinone; mp. 272.0° C. (interm. 27).

Workup

  1. additionthere was added
  2. filtrationThe precipitate was filtered off
  3. washwashed with water, 2-propanol and 1,1'-oxybisethane
  4. customdried

Sources & evidence

ORD record
ord-4698a5d77e14448aacc06dc26e19a6a9
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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