Acetic Anhydride → 2-Acetylamino-6-chloroisonicotinic acid ethyl ester

HRID 1664217Notes

Reaction equation

HRID 1664217 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH2:12])[CH:6]=1)[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH:12][C:14](=[O:16])[CH3:15])[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 269587Ethyl 2-amino-6-chloropyridine-4-carboxylate

Product 1

HCID 866204842-Acetylamino-6-chloroisonicotinic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 14 g 2-amino-6-chloro-isonicotinic acid ethyl ester (Temple et al. J. Heterocycl. Chem. 1970, 7, 451) (70 mmol) in 150 ml acetic anhydride (large excess) and 150 ml pyridine (large excess) is stirred at 60° C. in the presence of 244 mg (2 mmol) DMAP for 16 h. The mixture is concentrated in vacuo, taken up in EtOAc and washed with 1N HCl, brine and 10% aq Na2CO3 to yield the title compound in the form of yellowish crystals (EtOH).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washwashed with 1N HCl, brine and 10% aq Na2CO3

Sources & evidence

ORD record
ord-f9857cf0642b4e0194f39f5430c89e21
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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