Ethanol → Ethyl 2-amino-6-chloronicotinate

HRID 78175Notes

Reaction equation

HRID 78175 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].C(=O)([O-])O.[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([Cl:16])=[N:15][C:7]=1[NH2:6])[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 45926148Ethyl 2-amino-6-chloronicotinateYield 74%

Conditions

Temperature
65 °C

Procedure

To ethanol (20 mL) were added concentrated sulfuric acid (10 mL) and 2-amino-6-chloro-nicotinic acid (6.3 g, 27 mmol, purity: 75%) described in Manufacturing Example 26-1-1 on an ice bath, which was stirred overnight at 65° C. The reaction mixture was gradually cooled, after which a sodium hydrogencarbonate aqueous solution was added to neutralize the mixture. The precipitated solids were filtered to obtain the title compound (4.1 g, 74%).

Workup

  1. customdescribed in Manufacturing Example 26-1-1 on an ice bath
  2. temperatureThe reaction mixture was gradually cooled
  3. filtrationThe precipitated solids were filtered

Sources & evidence

ORD record
ord-863f6d4472c84b9287a6c62b77e522c3
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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