Hydrochloric Acid → HCID 14373257, compound

HRID 2081600Notes

Reaction equation

HRID 2081600 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[BH4-].[Na+].Cl>O.CO>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14373255120067-47-2

Product 1

HCID 14373257HCID 14373257, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 27.3 parts of intermediate 18, namely 6-benzoyl-3,4-dihydro-2(1H)-quinolinone, in 790 parts of methanol were added 115 parts of an aqueous sodium hydroxide solution 1N. After stirring for 10 min., there were added at once 4.54 parts of sodium tetrahydroborate. Stirring was continued over weekend at room temperature. There were added 110 ml of HCl 1N and 1000 parts of water. The precipitate was filtered off, stirred in water for 15 min and then taken up in a mixture of methanol and methylbenzene. This solution was evaporated and the residue was coevaporated with methylbenzene. The product was filtered off and dried at 70° C., yielding 21.9 parts (78.6%) of 3,4-dihydro-6-(hydroxyphenylmethyl)-2(1H)-quinolinone; mp. 175.0° C. (interm. 19). In a similar manner there were also prepared:

Workup

  1. stirringStirring
  2. waitwas continued over weekend at room temperature
  3. filtrationThe precipitate was filtered off
  4. stirringstirred in water for 15 min
  5. additiontaken up in a mixture of methanol and methylbenzene
  6. customThis solution was evaporated
  7. filtrationThe product was filtered off
  8. customdried at 70° C.

Sources & evidence

ORD record
ord-70f78123e55c478d988c73dac56c2b4c
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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