Hydrochloric Acid → HCID 21697092, compound

HRID 379019Notes

Reaction equation

HRID 379019 reaction equation
[OH:1][C:2]1[CH:16]=[C:15](I)[CH:14]=[CH:13][C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].Cl.[CH3:19][N:20](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:19]([C:15]1[CH:14]=[CH:13][C:3]([C:4]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:5])=[C:2]([OH:1])[CH:16]=1)#[N:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 21697088HCID 21697088, compound

Product 1

HCID 21697092HCID 21697092, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

A solution of phenyl 2-hydroxy-4-iodobenzoate, as described in Example 1, Step A, (2.38 g, 7.0 mmol) and Zn(CN)2 (575 mg, 4.9 mmol) in DMF was degassed with argon for 25 minutes. Pd(Ph3P)4 (404 mg, 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. customwas degassed with argon for 25 minutes
  2. extractionextracted with EtOAc (2×)
  3. washwashed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-f1397a6cfce4461db07428621fd0f34f
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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