Hydrochloric Acid → Methyl 6-acetyl-4-amino-3-methoxypicolinate

HRID 407247Notes

Reaction equation

HRID 407247 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]CC)=[CH2:9])[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:3]=1[O:17][CH3:18].Cl>C1COCC1>[C:8]([C:6]1[N:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:3]([O:17][CH3:18])=[C:2]([NH2:1])[CH:7]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86675416Methyl 4-amino-6-(1-ethoxyvinyl)-3-methoxypicolinate

Product 1

HCID 71150549Methyl 6-acetyl-4-amino-3-methoxypicolinateYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-amino-6-(1-ethoxyvinyl)-3-methoxypicolinate (1.68 g, 6.66 mmol) in THF (44.4 ml) was added a 2 N solution of hydrochloric acid (6.66 ml, 13.32 mmol). The milky solution was stirred at room temperature overnight. The clear yellow reaction mixture was concentrated. The residue was poured into saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, concentrated and dried in vacuo to afford methyl 6-acetyl-4-amino-3-methoxypicolinate (1.55 g, 6.91 mmol, 104% yield) as an orange solid which was used without further purification in the next step. ESIMS m/z 223 ([M−H]−); 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 4.59 (s, 2H), 4.01 (s, 3H), 3.90 (s, 3H), 2.67 (s, 3H).

Workup

  1. concentrationThe clear yellow reaction mixture was concentrated
  2. additionThe residue was poured into saturated NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-cbbf0ce0ddc64c4bbdae269652a5e72b
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

Loading…