Ammonia → HCID 10680039, compound

HRID 850167Notes

Reaction equation

HRID 850167 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C:21](OC)=[O:22])=[CH:17][N:16]=2)=[CH:9][CH:8]=1.N.CO>O1CCCC1>[OH:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15](/[CH:14]=[CH:13]/[C:10]2[CH:9]=[CH:8][N:7]=[CH:12][CH:11]=2)=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 10633779HCID 10633779, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10680039HCID 10680039, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (31.1 mg) in tetrahydrofuran (1 ml) was dropwise added a solution of methyl 2-[(E)-2-(4-pyridyl)vinyl]pyridine-5-carboxylate (385 mg) in tetrahydrofuran (10 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 45 minutes at the same temperature. Aqueous ammonia was dropwise added thereto at 0° C. and then methanol (5 ml) was further added thereto, and the mixture was stirred for 2 hours. After filtration the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with water and brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was washed with diisopropyl ether to give 5-hydroxymethyl-2-[(E)-2-(4-pyridyl)vinyl]pyridine (251 mg).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. filtrationAfter filtration the filtrate
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f20c93486c2f4e7c8d7c66af0f46b040
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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