Hydrochloric Acid → MS 857

HRID 1194496Notes

Reaction equation

HRID 1194496 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[C:17]([NH2:23])(=[O:22])[CH2:18][C:19]([CH3:21])=[O:20].Cl.N1C2C(=CC=CC=2)C=CC=1>CNC>[C:19]([C:18]1[C:17](=[O:22])[NH:23][C:1]([CH3:2])=[C:4]2[C:5]=1[CH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[CH2:9]2)(=[O:20])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 80077AcetoacetamideHCID 137720552-Acetyl-4-(4-pyridyl)cyclohexanone

Product 1

HCID 129517MS 857Yield 30.8%

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

In 40 ml of 50% aqueous solution of dimethylamine was dissolved 20 g of the 2-acetyl-4-(4-pyridyl)-cyclohexanone obtained by the above method (b) under ice cooling, and 30 g of acetoacetamide was added thereto. After stirring at room temperature for 2 days, the reaction mixture was neutralized with 6N hydrochloric acid under ice cooling. After allowed to stand for 1 hour under ice cooling, the resulting mixture was filtered to afford 12 g of crude crystals containing 3-4% of the above-said quinoline compound (IV) which was impurities. The crude crystals were recrystallized with 300 ml of methanol to afford 8 g of purified 4-acetyl-1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinone. The physical property values were as follows.

Workup

  1. customobtained by the above method (b) under ice cooling
  2. waitto stand for 1 hour under ice cooling
  3. filtrationthe resulting mixture was filtered
  4. customto afford 12 g of crude crystals
  5. customThe crude crystals were recrystallized with 300 ml of methanol

Sources & evidence

ORD record
ord-da53a3df5ab445b8b2d460d565329608
Source dataset
uspto-grants-1989_03
Patent number
US04814458

Reaction notes

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