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

HRID 599286Notes

Reaction equation

HRID 599286 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, from Example C3) in THF (40 mL) was added LiAlH4 (1.4 g, 37.4 mmol) portionwise under a 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-55afe23bff184cea85622906c76ea08d
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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