Dimethylamine → 2-Chloro-6-dimethylamino-isonicotinic acid tert-butyl ester

HRID 1908752Notes

Reaction equation

HRID 1908752 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([Cl:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][CH3:18]>C1COCC1>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11]([N:17]([CH3:18])[CH3:16])[N:10]=[C:9]([Cl:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 22594123tert-Butyl 2,6-dichloropyridine-4-carboxylate

Product 1

HCID 866405942-Chloro-6-dimethylamino-isonicotinic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A red to brown solution of 2,6-dichloro-isonicotinic acid tert.-butyl ester (1.49 g, 6.0 mmol) in 2 M dimethylamine in THF (20 mL) is stirred at 65° C. for 2 h, then at 80° C. for 2 h and finally at 110° C. for 12 h in an autoclave. The mixture is concentrated to give crude 2-chloro-6-dimethylamino-isonicotinic acid tert-butyl ester (2.0 g) as a brown residue; LC-MS: tR=1.08 min; [M+H]+=257.32; 1H NMR (D6-DMSO): δ 1.54 (s, 9H), 3.06 (s, 6H), 6.85 (s, 1H), 6.92 (s, 1H).

Workup

  1. waitfinally at 110° C. for 12 h in an autoclave
  2. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-20f2356508ae443b986d8cfeb0d7d3c1
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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