Water → HCID 21555652, compound

HRID 267220Notes

Reaction equation

HRID 267220 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=2)[N:5]=[C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=1.P(Cl)(Cl)([Cl:23])=O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=2)[N:5]=[C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178440678HCID 178440678, compound

Product 1

HCID 21555652HCID 21555652, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

126 parts of ethyl 4-hydroxy-6-n-butylquinoline-2-carboxylate, prepared as described in Example 2, and 213 parts of phosphorus oxychloride were stirred together. After the exothermic reaction had subsided the dark-coloured mixture was stored for 1 hour at room temperature then cooled to 0°C, diluted with 75 parts of ethanol to improve its mobility and subsequently added dropwise to 500 parts of ice and 1500 parts of water. The aqueous mixture was neutralised to pH 7 - 8 by addition of sodium carbonate when 133.2 parts of a light brown coloured crystalline solid separated out and were collected by filtration and dried. This material was purified by recrystillisation from about 380 parts of acetone (with carbon treatment) and yielded 100.8 gm. of ethyl 4-chloro-6-n-butylquinoline-2-carboxylate which was isolated as pale grey needles, m.pt. 58°- 58.5°C. An additional 27.5 parts of less pure product, m.pt. 54.5°-56°C, was obtained by dilution of the acetone mother-liquor with water.

Workup

  1. customAfter the exothermic reaction
  2. customseparated out
  3. filtrationwere collected by filtration
  4. customdried
  5. customThis material was purified by recrystillisation from about 380 parts of acetone (with carbon treatment)
  6. customyielded 100.8 gm

Sources & evidence

ORD record
ord-b710d25a982a499991d1b652a66ed7f2
Source dataset
uspto-grants-1976_03
Patent number
US03941793

Reaction notes

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