Water → HCID 12367723, compound

HRID 436261Notes

Reaction equation

HRID 436261 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][CH2:14][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=[O:16].[OH2:20].[OH-:21].[K+]>CO>[OH:20][N:5]1[C:6]2[CH:7]=[C:8]3[CH2:14][CH2:13][O:12][C:9]3=[CH:10][C:11]=2[C:2](=[O:21])[C:3]([C:15]([OH:17])=[O:16])=[CH:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 21453925HCID 21453925, compound

Product 1

HCID 12367723HCID 12367723, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture containing 12 g of ethyl 8-chloro-2,3-dihydrofuro(2,3-g)quinoline-7-carboxylate, 100 ml of water, 10.9 g of 85% potassium hydroxide and 80 ml of methanol was stirred while refluxing for 2 hours. The methanol was evaporated at atmospheric pressure. The resulting mixture was heated to 90°-95° C and stirred for one further hour. Then, the mixture was acidified to pH 2 by the addition of 6N hydrochloric acid at 80° C. After cooling, the resulting white precipitate was filtered and washed with water to give 10.03 g (99%) of 2,3,5,8-tetrahydro-5-hydroxy-8-oxofuro(2,3-g)-quinoline-7-carboxylic acid as pale yellow prisms having a melting point of 274°-275° C (decomposition). Elementary analysis values for C12H9O5N were as follows:

Workup

  1. temperaturewhile refluxing for 2 hours
  2. customThe methanol was evaporated at atmospheric pressure
  3. temperatureThe resulting mixture was heated to 90°-95° C
  4. stirringstirred for one further hour
  5. additionThen, the mixture was acidified to pH 2 by the addition of 6N hydrochloric acid at 80° C
  6. temperatureAfter cooling
  7. filtrationthe resulting white precipitate was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-378957b56f7a4dc5b443b09089f4cc7a
Source dataset
uspto-grants-1977_02
Patent number
US04008237

Reaction notes

Loading…