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Hydrochloric Acid → Methyl 4-cyano-3-hydroxybenzoate

HRID 379022
Notes
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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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06297239B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes