Water → HCID 20399854, compound

HRID 1981137Notes

Reaction equation

HRID 1981137 reaction equation
[CH3:1][O-:2].[Na+].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1)=[O:11].O>CO>[CH3:1][O:2][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 13472122HCID 13472122, compound

Product 1

HCID 20399854HCID 20399854, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.8 g) was added to a solution of 1-(6-bromohexanoyl)-1,2,3,4-tetrahydroquinoline (2.1 g) in methanol (50 ml). The mixture was refluxed for 8 hours, then poured into water and extracted with ether. The extract was dried and evaporated and the residue chromatographed on silica gel, eluting with 98:2 methylene chloride:methanol, so as to obtain the product 1-(6-methoxyhexanoyl)-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. extractionextracted with ether
  3. customThe extract was dried
  4. customevaporated
  5. customthe residue chromatographed on silica gel
  6. washeluting with 98:2 methylene chloride

Sources & evidence

ORD record
ord-e81274a51acd4ec5b408b04c4914d690
Source dataset
uspto-grants-1985_04
Patent number
US04512990

Reaction notes

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