Dimethylformamide → HCID 131716995, compound

HRID 727792Notes

Reaction equation

HRID 727792 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[CH:9]([CH2:10][C:11](=[O:21])[N:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[N:13]=3)[CH2:8][CH2:7][C:6]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>O>[ClH:34].[ClH:34].[O:41]1[CH2:42][CH2:43][N:38]([CH2:37][CH2:36][CH2:35][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:14]4[CH:9]([CH2:10][C:11](=[O:21])[N:12]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=5)[N:13]=4)[CH2:8][CH2:7][C:6]=3[CH:22]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 135816633HCID 135816633, compound

Product 1

HCID 131716995HCID 131716995, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of 1.4 g of 8-hydroxy-2-(2-pyridyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one, 1.4 g of potassium carbonate and 30 ml of dimethylformamide is added 1.3 g of N-(3-chloropropyl)morpholine, and the mixture is stirred at 55° C. for 3 hours. After the completion of the reaction, water is added to the reaction mixture and the mixture is extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure. The obtained oily substance is purified by silica gel column chromatography (chloroform : methanol =10 : 1) and converted into the hydrochloride in methanol, which is recrystallized from methanol to give 0.6 g of 8-(3-morpholinopropoxy)-2-(2-pyridyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one. dihydrochloride.dihydrate as white crystals, m.p. 201°-202° C. (decomposition).

Workup

  1. additionis added to the reaction mixture
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customThe obtained oily substance is purified by silica gel column chromatography (chloroform : methanol =10 : 1)
  7. customis recrystallized from methanol

Sources & evidence

ORD record
ord-7cffa23dfa6944f0861fcf7c37eb8a1c
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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