Sulfuric Acid → HCID 86734551, compound

HRID 597045Notes

Reaction equation

HRID 597045 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([O:26][CH2:27]C)=[O:25])=[C:13]3[CH3:29])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>CO>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([C:6]1[C:5]3[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=1)[C:13]([CH3:29])=[C:14]2[CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 21449365HCID 21449365, compound

Product 1

HCID 86734551HCID 86734551, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxy-2-methyl-1-quinol-4-ylindol-3-ylacetic acid (2g.) in methanol (30ml.) containing concentrated sulphuric acid (1 ml.) was refluxed for 2 hours. The resulting red solution was treated with saturated methanolic sodium acetate solution (30ml.) and the methanol then evaporated in vacuo. The residue was diluted with water (50ml.) and extracted with diethyl ether (2 × 30ml.). The ether extracts were dried (MgSO4) and evaporated, to yield methyl 5-methoxy-2-methyl-1-quinol-4-ylindol-3-ylacetate, m.p. 103°-105° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe methanol then evaporated in vacuo
  3. additionThe residue was diluted with water (50ml.)
  4. extractionextracted with diethyl ether (2 × 30ml.)
  5. dry with materialThe ether extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5731b5be9972427d85f8c417a384e800
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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