Hydrochloric Acid → HCID 19384469, compound

HRID 2399805Notes

Reaction equation

HRID 2399805 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[CH:13][CH:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:15]3[C:19]=2[N:18]=[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=32)[O:6]1)=[O:4].[OH-].[Na+].Cl>O1CCCC1.CO.O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:14]2[C:15]3=[C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:17]4=[N:18][C:19]3=[C:11]([O:10][C:7]3[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)[CH:12]=[CH:13]2)=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53967837HCID 53967837, compound

Product 1

HCID 19384469HCID 19384469, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-[[9-[(4-fluorophenyl)methyl]-1,2,3,4-tetrahydro-9H-dibenzo[b,d]pyrrol-6-yl]oxy]-2-furancarboxylic acid methyl ester (2.1 g) from Example 123 in tetrahydrofuran (20 mL) and methanol (10 mL) was treated with 1N sodium hydroxide solution (6 mL) and refluxed for 90 minutes. The reaction mixture was diluted with water, treated with excess 2N hydrochloric acid (4 mL) and the product extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, evaporated in vacuo, and crystallized from dichloromethane-hexane to provide 1.7 g (84%) of 5-[[9-[(4-fluorophenyl)methyl]-1,2,3,4-tetrahydro-9H-dibenzo[b,d]pyrrol-6-yl]oxy]-2-furancarboxylic acid as a colorless crystalline material, mp at 161° C. with decomposition.

Workup

  1. temperaturerefluxed for 90 minutes
  2. extractionthe product extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-6e4a4bfe399940f087de4183c2bc15cf
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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