Methanol → HCID 67469370, compound

HRID 630419Notes

Reaction equation

HRID 630419 reaction equation
[NH2:1][C:2]1[C:11](I)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[C:15]([Zn]C#N)#[N:16].O.CO>CN(C)C=O.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.CCOCC>[NH2:1][C:2]1[C:11]([C:15]#[N:16])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 15700587Methyl 4-amino-5-iodo-2-methoxybenzoate2×HCID 178514179HCID 178514179, compound

Product 1

HCID 67469370HCID 67469370, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of methyl 4-amino-5-iodo-2-methoxybenzoate (intermediate 128; 5 g, 16.28 mmol) and dicyanozinc (1.5 g, 12.77 mmol) in dimethylformamide (50 mL) in a slenck vessel was degasified with nitrogen. Then tetrakis (1 g, 0.87 mmol) was added and the reaction mixture was stirred at 80° C. for 2 hours. Water was added into the reaction mixture and the crude was extracted with ethyl acetate, the organic layer was washed with brine, dried and the solvent was removed under reduced pressure. The crude obtained was treated with methanol and ether to obtain the title compound as a yellow solid (76%).

Workup

  1. extractionthe crude was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe crude obtained

Sources & evidence

ORD record
ord-4c12ff883106411f8551a7e0b8f78730
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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