Citric Acid → HCID 59654927, compound

HRID 1497730Notes

Reaction equation

HRID 1497730 reaction equation
[NH2:1][C:2]1[C:7]([C:8](N(OC)C)=[O:9])=[CH:6][C:5]([Cl:14])=[N:4][CH:3]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OCC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:9])=[CH:6][C:5]([Cl:14])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 105612979HCID 105612979, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 59654927HCID 59654927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 5-Amino-2-chloro-N-methoxy-N-methyl-isonicotinamide (1.50 g, 6.608 mmol) in THF (25 mL) under argon is added phenylmagnesium bromide in diethyl ether (6.00 mL, 2M, 18 mmol) at 0° C. The mixture is stirred for 30 minutes at 0° C. Aqueous citric acid solution (1 M, 25 mL) is added to the reaction and the mixture is extracted with ethyl acetate, the organic phase is dried over magnesium sulfate. The drying agent is removed by filtration and the solvent is concentrated to dryness. This provides the desired compound which is used without further purification.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customThe drying agent is removed by filtration
  4. concentrationthe solvent is concentrated to dryness

Sources & evidence

ORD record
ord-89aa4279c0a546d9ab5a022fd20be283
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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