Isonicotinic Acid → HCID 4137929, compound

HRID 476626Notes

Reaction equation

HRID 476626 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][NH:11]1>O1CCCC1>[N:5]1[CH:4]=[CH:3][C:2]([C:1]([N:11]2[CH2:12][CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10]2)=[O:9])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 70461,2,3,4-Tetrahydroisoquinoline

Product 1

HCID 4137929HCID 4137929, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 g (406 mmol) of isonicotinic acid are dissolved under an argon atmosphere in 1000 ml of tetrahydrofuran and 25 g of N,N'-carbonyldiimidazole are added while stirring, the mixture is stirred for half an hour, a further 25 g of N,N'-carbonyldiimidazole are added, the mixture is stirred for a further half hour and 15 g of N,N'-carbonyldiimidazole are added. Stirring is continued for 1 h 30 min, 51.39 g (385.8 mmol) of 1,2,3,4-tetrahydroisoquinoline dissolved in a few millilitres of tetrahydrofuran are introduced slowly into the mixture, which has become clear, and the mixture is stirred overnight at room temperature. The solvent is then evaporated off, the oily residue taken up with approiximately 700 ml of dichloromethane, and the solution obtained washed twice with saturated sodium bicarbonate solution and thereafter twice with water and dried over magnesium sulphate. 87.48 g of an orange-coloured oil, which solidifies slowly in the cold, are obtained.

Workup

  1. stirringthe mixture is stirred for half an hour
  2. stirringthe mixture is stirred for a further half hour
  3. stirringStirring
  4. additionare introduced slowly into the mixture, which
  5. stirringthe mixture is stirred overnight at room temperature
  6. customThe solvent is then evaporated off
  7. customthe solution obtained
  8. washwashed twice with saturated sodium bicarbonate solution
  9. dry with materialtwice with water and dried over magnesium sulphate
  10. customare obtained

Sources & evidence

ORD record
ord-d4b6b8dec33f49b282b161286f76e093
Source dataset
uspto-grants-1989_12
Patent number
US04885302

Reaction notes

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