Aluminium lithium hydride → (6-Chloro-4-(phenylamino)pyridin-3-yl)methanol

HRID 1930298Notes

Reaction equation

HRID 1930298 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59212513Ethyl 6-chloro-4-(phenylamino)nicotinate

Product 1

HCID 86620159(6-Chloro-4-(phenylamino)pyridin-3-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 6-chloro-4-(phenylamino)nicotinate (19 g, 89 mmol) in anhydrous THF (40 mL) was added dropwise to a 0° C. suspension of LiAlH4 (8.5 g, 223 mmol) in anhydrous THF (80 mL). After complete addition, the reaction mixture was stirred at RT for 3 h. The mixture was quenched by the addition of 10% aq NaOH (8.5 mL) and water (8.5 mL). The solids were removed by filtration and the organic phase was concentrated in vacuo to provide (6-chloro-4-(phenylamino)pyridin-3-yl)methanol (12 g, 80% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.09 (s, 1 H), 8.08 (s, 1 H), 7.39-7.10 (m, 5 H), 6.73 (s, 1 H), 5.37 (s, 1 H), 4.52 (s, 2 H).

Workup

  1. additionAfter complete addition
  2. customThe mixture was quenched by the addition of 10% aq NaOH (8.5 mL) and water (8.5 mL)
  3. customThe solids were removed by filtration
  4. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-f1b904f616e3484d8478d587d137a598
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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