Citric Acid → HCID 21109706, compound

HRID 1766504Notes

Reaction equation

HRID 1766504 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[C:7](Cl)=[N:6][CH:5]=1.[CH3:13][O:14][CH2:15][CH2:16][NH:17][CH3:18].[OH-].[Na+].Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N12CCCN=C1CCCCC2>[Br:10][C:8]1[C:7]([N:17]([CH2:16][CH2:15][O:14][CH3:13])[CH3:18])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:2])=[O:12]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 300977(2-Methoxyethyl)(methyl)amineHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 21109706HCID 21109706, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 5-bromo-6-chloro-nicotinic acid methyl ester (1 g) and N-(2-methoxyethyl)methylamine (0.89 g) in 1,8-diazabicyclo[5.4.0]undec-7-ene (1.519 g) was stirred at 60° C. for 3 h and at 90° C. for 1 h. 2 M NaOH (3.99 ml) was added and the mixture was stirred at 90° C. for 15 min. After cooling to room temperature 2 M HCl (3.99 ml) was added. The mixture was acidified using concentrated citric acid solution. The mixture was extracted with ethyl acetate. The org. phase was washed with brine, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1) to give 5-bromo-6-[(2-methoxy-ethyl)-methyl-amino]-nicotinic acid (1.06 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at 90° C. for 15 min
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washphase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-1a3ff04ab9194d239635713888247f1e
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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