Hydrochloric Acid → Methyl 4-cyano-3-hydroxybenzoate

HRID 379022Notes

Reaction equation

HRID 379022 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].Cl.[CH3:14][N:15](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[C:14]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])#[N:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A solution of methyl 3-hydroxy-4-iodobenzoate (2.38 g, 7.0 mmol) (as described in Step B) and Zn(CN)2 (0.575 g, 4.9 mmol) in DMF was degassed with argon for 25 minutes. Pd(Ph3P)4 (0.404 g, 0.35 mmol) was added and the mixture heated to 80° C. for 16 hr. The mixture was poured into 1N HCl and extracted with EtOAc (2×), washed with water then brine, dried (MgSO4) and the solvent removed. Chromatography of the residue (silica gel; hexane:EtOAc 9:1) afforded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washwashed with water
  3. dry with materialbrine, dried (MgSO4)
  4. customthe solvent removed

Sources & evidence

ORD record
ord-91c476a90c244af79776c2ac6b291680
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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