HCID 54010783, compound → HCID 21449402, compound

HRID 597056Notes

Reaction equation

HRID 597056 reaction equation
[Cl:1][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)[CH:14]([CH2:23][C:24](O)=[O:25])[CH:13]3[CH3:27])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>CO>[Cl:1][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][CH2:24][OH:25])=[C:13]3[CH3:27])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54010783HCID 54010783, compound2×

Product 1

HCID 21449402HCID 21449402, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindol-3-ylacetate (1g.) and sodium borohydride (1g.) in methanol (30ml.) were refluxed for 1 hour. Most of the methanol was then removed in vacuo, and the residue was diluted with water (50ml.), and extracted with ethyl acetate (3 × 50ml.). The combined extracts were dried (MgSO4) and evaporated to give an oil, which was chromatographed on silica gel (100g.) using, as eluant, petroleum ether (b.p. 40°-60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether) to give 1-(7-chloroquinol-4-yl)-3-(2-hydroxyethyl)-5-methoxy-2-methylindole, m.p. 143°-145° C.

Workup

  1. customMost of the methanol was then removed in vacuo
  2. additionthe residue was diluted with water (50ml.)
  3. extractionextracted with ethyl acetate (3 × 50ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customto give an oil, which
  7. customwas chromatographed on silica gel (100g.)
  8. additionpetroleum ether (b.p. 40°-60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether)

Sources & evidence

ORD record
ord-847ad5aa50ac499dbd7e8b6a05c70743
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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