Nitrogen → (6-Chloro-4-(methylamino)pyridin-3-yl)methanol

HRID 1930398Notes

Reaction equation

HRID 1930398 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH3:14])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:11]([NH:13][CH3:14])[CH:12]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 20627001Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 51000240(6-Chloro-4-(methylamino)pyridin-3-yl)methanolYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of ethyl 6-chloro-4-(methylamino)nicotinate (4 g, 18.7 mmol) in THF (40 mL) was added LiAlH4 (1.4 g, 37.4 mmol) portionwise under N2 atmosphere. After stirring for 20 min, the reaction was quenched by cautious addition of water followed by aqueous solution of 2 N NaOH. The suspension was filtered and the filtrate was concentrated to afford (6-chloro-4-(methylamino)pyridin-3-yl)methanol (2.9 g, 90.6% yield), which was used in next step without purification. 1HNMR (400 MHz, DMSO-d6): δ 7.96 (s, 1 H), 6.63 (s, 1 H), 6.46 (s, 1 H), 5.04 (s, 1 H), 4.39 (m, 2 H), 2.81-2.68 (m, 3 H).

Workup

  1. customthe reaction was quenched by cautious addition of water
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0839917b5a554a9382e82538243451f8
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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