Water → 2-Amino-6-vinyl-nicotinic acid methyl ester

HRID 2079949Notes

Reaction equation

HRID 2079949 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][C:5]=1[NH2:11].[CH:13]([Sn](CCCC)(CCCC)CCCC)=[CH2:14].O.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:13]=[CH2:14])=[N:6][C:5]=1[NH2:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 57415887Methyl 2-amino-6-chloronicotinate

Product 1

HCID 583190542-Amino-6-vinyl-nicotinic acid methyl esterYield 66.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

2-Amino-6-chloro-nicotinic acid methyl ester (2.95 g, 15.8 mmol), vinyl tri-n-butyltin (5.01 g, 15.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.83 g, 1.58 mmol) were suspended in xylene (15 mL), and heated for 1 hour at 130° C. The reaction mixture was allowed to room temperature, water and ethyl acetate were added thereto, this mixture was filtered through Celite pad, then, the filtrate thereof was partitioned. The organic layer was separated, the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (1.87 g, 10.5 mmol, 66%) as a white solid.

Workup

  1. customwas allowed to room temperature
  2. filtrationthis mixture was filtered through Celite pad
  3. customthe filtrate thereof was partitioned
  4. customThe organic layer was separated
  5. customthe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8deadf02ce9f4666b71ea4b71031975b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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