Dimethyl acetylenedicarboxylate → HCID 70549271, compound

HRID 1065073Notes

Reaction equation

HRID 1065073 reaction equation
C([NH:3][C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:7](CCC)=[C:6](O)[CH:5]=1)C.[C:18]([C:24](OC)=O)#[C:19][C:20]([O:22][CH3:23])=[O:21]>[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO>[CH3:23][O:22][C:20]([CH:19]1[CH2:18][CH2:24][C:5]2[C:4](=[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=2)[NH:3]1)=[O:21]

Participants

5

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 20541323HCID 20541323, compound

Product 1

HCID 70549271HCID 70549271, compound

Reagents, catalysts & solvents 2

HCID 66854Benzyltrimethylammonium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Benzyltrimethylammonium hydroxide (40% aqueous solution) (3 drops) was added to a stirred solution of 1-ethylamino-3-hydroxy-4-propyl-5,6,7,8-tetrahydronaphthalene (2.33 g) and dimethyl acetylene dicarboxylate (1.42 g) in methanol (10 ml). The mixture was heated at reflux for 8 hours, cooled, filtered and the methanol removed in vacuo. The resulting oil, a mixture of the cis and trans tetrahydronaphthylamino acrylic acid esters, was heated on a steam bath with polyphosphoric acid (10 g) for 2 hours. The mixture was cooled, poured into water and the solution adjusted to pH7 with sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The extracts were dried (magnesium sulphate) and evaporated in vacuo giving crude tetrahydrobenzo quinoline-2-carboxylic acid methyl ester as a sticky solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe methanol removed in vacuo
  6. additionThe resulting oil, a mixture of the cis and trans tetrahydronaphthylamino acrylic acid esters
  7. temperaturewas heated on a steam bath with polyphosphoric acid (10 g) for 2 hours
  8. temperatureThe mixture was cooled
  9. additionpoured into water
  10. extractionThe resulting mixture was extracted with ethyl acetate
  11. dry with materialThe extracts were dried (magnesium sulphate)
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-7a59ef9786864e378404d9f9f969ef98
Source dataset
uspto-grants-1982_05
Patent number
US04328230

Reaction notes

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