Sodium Hydroxide → HCID 14576176, compound

HRID 232142Notes

Reaction equation

HRID 232142 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:13]2[CH2:14][CH2:15][CH2:16][C:12]=2[N:11]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[N:10]=1.[OH-].[Na+]>CO>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([N:11]2[C:12]3[CH2:16][CH2:15][CH2:14][C:13]=3[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2])=[N:10]2)=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14576173HCID 14576173, compound

Product 1

HCID 14576176HCID 14576176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-[1-(4-nitrophenyl)-1,4,5,6-tetrahydro-3-cyclopentapyrazolyl]hexanoic acid methyl ester (see Example 18) (0.07 g) in methanol (10 ml) was treated with 2N sodium hydroxide (2 ml) and heated at reflux temperature for 45 minutes. The solution was cooled, evaporated, diluted with water and acidified. The precipitate was extracted into ethyl acetate, washed with 5% saline, dried, and evaporated. The residue was filtered through CC-4 silica gel to remove polar impurities, and the 25% ethyl acetate in hexane effluent gave pure title compound, m.p. 131°-132° C., after ethanol-water recrystallization.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 45 minutes
  3. temperatureThe solution was cooled
  4. customevaporated
  5. additiondiluted with water
  6. extractionThe precipitate was extracted into ethyl acetate
  7. washwashed with 5% saline
  8. customdried
  9. customevaporated
  10. filtrationThe residue was filtered through CC-4 silica gel
  11. customto remove polar impurities
  12. customthe 25% ethyl acetate in hexane effluent gave pure title compound, m.p. 131°-132° C., after ethanol-water recrystallization

Sources & evidence

ORD record
ord-675aae791686431bb63aa7865f248907
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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