Ammonium Chloride → HCID 58001792, compound

HRID 420697Notes

Reaction equation

HRID 420697 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10](OCC)=[O:11])=[CH:6][CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.CC(C)([O-])C.[K+].[NH4+].[Cl-]>C1COCC1>[CH3:16][O:15][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][CH2:9][C:10](=[O:11])[NH:1][C:2]=2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 58001786HCID 58001786, compound

Product 1

HCID 58001792HCID 58001792, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl N-[2-amino-6-(methyloxy)-3-pyridinyl]glycinate (40.6 g, 135 mmol) was dissolved in THF (1 L) at room temperature under argon and treated with potassium tert-butoxide (15.17 g, 135 mmol). After 2 h at room temperature saturated NH4Cl (500 ml) was added and the THF evaporated. Water (500 ml) was added followed by 20% MeOH/DCM (1 L); the insoluble material was filtered off, washed with Et2O and dried in the vacuum oven at 40° C. overnight to afford the desired product as a yellow solid (15.3 g): LCMS and NMR consistent with product (9% of oxidized material present by NMR).

Workup

  1. customthe THF evaporated
  2. additionWater (500 ml) was added
  3. filtrationthe insoluble material was filtered off
  4. washwashed with Et2O
  5. customdried in the vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-992ee380e681426fbd1380d14701bd8d
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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