Lithium hydroxide, monohydrate → Lithium 2-amino-5-chloronicotinate

HRID 221420Notes

Reaction equation

HRID 221420 reaction equation
O[Li:2].O.[NH2:4][C:5]1[N:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>O.CO>[NH2:4][C:5]1[N:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:6]=1[C:7]([O-:9])=[O:8].[Li+:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15828199Methyl 2-amino-5-chloronicotinate

Product 1

HCID 66841695Lithium 2-amino-5-chloronicotinateYield 114.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of LiOH.H2O (1.38 g, 33 mmol) in water (33 mL) was added in one portion to a suspension of methyl 2-amino-5-chloronicotinate (6.08 g, 27 mmol) in MeOH (110 mL). The reaction mixture was stirred at 70° C. for 24 hours, and gradually became homogeneous. The solvents were removed under reduced pressure, and after the resulting white solid was dried under vacuum (<1 mmHg) to constant weight, 5.51 g (95%) of lithium 2-amino-5-chloronicotinate was obtained.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customafter the resulting white solid was dried under vacuum (<1 mmHg) to constant weight

Sources & evidence

ORD record
ord-fe01ce1346824cb68d1633ea08b632b1
Source dataset
uspto-grants-2012_06
Patent number
US08207170B2

Reaction notes

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