N-Methylethylamine → HCID 66935970, compound

HRID 1908789Notes

Reaction equation

HRID 1908789 reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([Cl:12])[C:9](Cl)=[N:8][CH:7]=1)([CH3:3])[CH3:2].[CH2:15]([NH:17][CH3:18])[CH3:16]>CC(=O)OCC>[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([N:17]([CH2:15][CH3:16])[CH3:18])=[N:8][CH:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 21836299HCID 21836299, compound

Product 1

HCID 66935970HCID 66935970, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5,6-dichloro nicotinic acid isopropyl ester (4.76 g, 22.3 mmol) and ethylmethylamine (6.88 g, 116.4 mmol) is stirred in a sealed vessel at 105° C. for 72 h. The mixture is cooled to rt, diluted with EA (300 mL) and washed with sat. aq. NaHCO3-solution (3×10 mL) followed by brine (10 mL). The org. extract is dried over MgSO4, filtered, concentrated and dried to give 5-chloro-6-(ethyl-methyl-amino)-nicotinic acid isopropyl ester (5.18 g) as a yellow oil; LC-MS: tR=1.38 min, [M+1]+=257.02; 1H NMR (D6-DMSO): δ 1.19 (t, J=6.8 Hz, 3H), 1.30 (d, J=6.0 Hz, 6H), 3.08 (s, 3H), 3.55 (q, J=7.0 Hz, 2H), 5.10 (hept, J=6.3 Hz, 1H), 7.98 (s, 1H), 8.58 (s, 1H).

Workup

  1. temperatureThe mixture is cooled to rt
  2. washwashed with sat. aq. NaHCO3-solution (3×10 mL)
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-c570ad3177674319a93336ffc73a34df
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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