Hydrochloric Acid → HCID 19101731, compound

HRID 1974564Notes

Reaction equation

HRID 1974564 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][CH2:23][CH2:24][C:25]([O:27]CC3C=CC=CC=3)=[O:26])=[CH:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:14]2)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19101742HCID 19101742, compound

Product 1

HCID 19101731HCID 19101731, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of benzyl 4-[1-(3-nitrobenzenesulfonyl)indol-3-yl]butyrate (1.95 g) in 1,4-dioxane (15 ml) was added 1N-sodium hydroxide (8 ml). The mixture was stirred for 2 hours and poured into diluted hydrochloric acid. The organic layer was extracted with ethyl acetate (30 ml) and washed with water (30 ml×3). The solution was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was crystallized with diisopropyl ether to give a yellow solid of 4-[1-[3-nitrobenzenesulfonyl)indol-3-yl]butyric acid (1.45 g).

Workup

  1. extractionThe organic layer was extracted with ethyl acetate (30 ml)
  2. washwashed with water (30 ml×3)
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-b3ef27884221496aad3e2e7a78c9c685
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

Loading…