Aluminium lithium hydride → HCID 59187380, compound

HRID 1948573Notes

Reaction equation

HRID 1948573 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=2[O:12][CH3:13])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOC(C)=O.O.[OH-].[Na+]>[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][NH2:11])[CH:7]=[CH:6][C:5]=2[O:12][CH3:13])[CH2:2][CH2:3]1

Participants

7

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57484710HCID 57484710, compound

Product 1

HCID 59187380HCID 59187380, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 6-cyclopropyl-5-methoxypyridine-2-carbonitrile (5-5, 115 mg, 0.66 mmol, 1 equiv) in THF (2.6 mL) at 0° C. was added LAH (1M, 1.98 mL, 1.98 mmol, 3 equiv) slowly. The reaction mixture was stirred and allowed to warm to ambient temperature over 3 hours. The reaction mixture was then diluted with EtOAc (2 mL), and water (50 uL), NaOH (aq., 20 wt. %, 50 uL) and water (100 uL) were added sequentially. The reaction mixture was then dried over MgSO4, filtered and concentrated to afford the product (5-6). ESI+ MS [M+H]+ C10H15N2O: 179.1 found, 179.2 required.

Workup

  1. additionwere added sequentially
  2. dry with materialThe reaction mixture was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-673d8dfdd8fb4c08bb29cc266f07f29a
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

Loading…