Ethyl 6-amino-5-bromonicotinate → (6-Amino-5-bromopyridin-3-yl)methanol

HRID 1684930Notes

Reaction equation

HRID 1684930 reaction equation
[NH2:1][C:2]1[C:12]([Br:13])=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:11][C:12]=1[Br:13]

Participants

4

Reactant 2

HCID 7210833Ethyl 6-amino-5-bromonicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 67263286(6-Amino-5-bromopyridin-3-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-amino-5-bromonicotinate (2.31 g, 10 mmol) in tetrahydrofuran (20 mL) at RT was added LAH (10 mL, 1M in tetrahydrofuran) dropwise. After stirring for 1 h, the mixture was quenched with water (0.2 mL) and the resultant precipitate was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford (6-amino-5-bromopyridin-3-yl)methanol (2.0 g, 99%) as a solid. LC/MS; (M+H)+=203, 205 (1:1 ratio). 1H NMR (CD3OD, 300 MHz) δ 7.79 (s, 1H), 7.67 (s, 1H), 4.35 (br S, 2H).

Workup

  1. customthe mixture was quenched with water (0.2 mL)
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-866511e5c528458cbc2c966f92d0c902
Source dataset
uspto-grants-2012_04
Patent number
US08148361B2

Reaction notes

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