Hydrochloric Acid → 5-(Hydroxymethyl)pyridine-2-carboxylic acid

HRID 851968Notes

Reaction equation

HRID 851968 reaction equation
[Li+].[BH4-].C[O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1)=O.Cl>C1COCC1>[OH:4][CH2:5][C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 4148881Lithium borohydride

Product 1

HCID 135185635-(Hydroxymethyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of LiBH4 (1.53 g, 70 mmol) in THF (30 ml) was slowly added to a solution of pyridine-2,5-dicarboxylic acid 5-methyl ester (2.5 g, 14 mmol) in dry THF (30 ml) at 0° C. and under an argon atmosphere. The reaction mixture was stirred for a further 2 h at r.t., then chilled to 0° C. and treated with 2 N HCl (40 ml). The reaction mixture was filtered, concentrated under reduced pressure and crystallized from MeOH: 340 mg;

Workup

  1. temperaturechilled to 0° C.
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from MeOH

Sources & evidence

ORD record
ord-8c97459139774be39779c6e97048d0e5
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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