Isonicotinic Acid → HCID 4137929, compound

HRID 2166371Notes

Reaction equation

HRID 2166371 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 milliliters 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 approximately 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-38aa82ecbc5744ac9ac89828a78007c0
Source dataset
uspto-grants-1990_07
Patent number
US04945096

Reaction notes

Loading…