Aluminium lithium hydride → HCID 58009138, compound

HRID 1430458Notes

Reaction equation

HRID 1430458 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH2:14][CH3:15])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:11]([NH:13][CH2:14][CH3:15])[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58009151HCID 58009151, compound

Product 1

HCID 58009138HCID 58009138, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A −50° C. solution of ethyl 6-chloro-4-(ethylamino)nicotinate (3.9 g, 17 mmol) in THF (50 mL) was treated with LiAlH4 (3.6 g, 95 mmol), allowed to warm to 0° C. and stirred for 1 h. The mixture was quenched with 10% NaOH (3.6 mL), filtered and the filtrate treated with water and extracted with EtOAc (3×). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to provide (6-chloro-4-(ethylamino)pyridin-3-yl)methanol (2.5 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (s, 1H), 6.55 (s, 1H), 6.17 (m, 1H), 5.25 (t, J=5.2 Hz, 1H), 4.44 (q, J=7.2 Hz, 2H), 3.23 (m, 2H), 1.23 (t, J=7.2 Hz, 3H).

Workup

  1. customThe mixture was quenched with 10% NaOH (3.6 mL)
  2. filtrationfiltered
  3. additionthe filtrate treated with water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-512a0e942f83458ea7604de4fc5adf82
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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