Sulfuric Acid → 1649468-09-6

HRID 1089440Notes

Reaction equation

HRID 1089440 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#N)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:24].[Na].[BH4-].[Na+]>CO.C(O)(=O)C.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:24])=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 21225700DiisobutylaluminumhydrideHCID 221593512-(6-Chloropyridin-3-yl)-2-methylpropanenitrile

Product 1

HCID 221593551649468-09-6

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3.6 g (20 mmol) of 2-(6-chloro-pyrid-3-yl)-2-methylpropionitrile are introduced into 50 ml of toluene, and 25 ml of a diisobutylaluminum hydride solution (1M in toluene) is added dropwise without cooling, by means of which the internal temperature rises to 45° C. The mixture is stirred for 2 hours at room temperature. 10 ml of methanol, 50 ml of water and 90 ml of 2N sulfuric acid are then cautiously added successively, and the mixture is stirred for 2 hours at room temperature and finally for 2 hours at 50° C. The toluene phase is separated off and the solvent is removed. The residue is dissolved in 10 ml of methanol and a solution of 0.1 g of sodium and 0.4 g (10.6 mmol) of sodium borohydride in 10 ml of methanol are added. The mixture is stirred for 1 hour at room temperature and acidified with 0.7 g of acetic acid, and the solvent is removed. The residue is boiled with ethyl acetate, the ester phase is boiled off and the solvent is removed in vacuo. The oily crude product is distilled in a bulb tube; 0.15 mbar, apparatus temperature 170° C. Yield 2.5 g (67% of theory) of a colorless oil.

Workup

  1. additionis added dropwise
  2. temperaturewithout cooling, by means of which the internal temperature
  3. customrises to 45° C
  4. stirringthe mixture is stirred for 2 hours at room temperature and finally for 2 hours at 50° C
  5. customThe toluene phase is separated off
  6. customthe solvent is removed
  7. dissolutionThe residue is dissolved in 10 ml of methanol
  8. stirringThe mixture is stirred for 1 hour at room temperature
  9. customthe solvent is removed
  10. customthe solvent is removed in vacuo
  11. distillationThe oily crude product is distilled in a bulb tube
  12. custom0.15 mbar, apparatus temperature 170° C

Sources & evidence

ORD record
ord-9952708dded2404aa152125b43bf28be
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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