Hydrogen iodide → 2-Iodo-5-phenylpyridine

HRID 892565Notes

Reaction equation

HRID 892565 reaction equation
C(C1C=CC2OC(C)(C)C=C([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][N+:15]=3[O-])C=2C=1)#N.ClC1C=CC(C2C=CC=CC=2)=CN=1.[IH:41]>>[I:41][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 24841Hydrogen iodideHCID 27628682-Chloro-5-phenylpyridineHCID 539962652-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-phenylpyridine N-oxide

Product 1

HCID 112197482-Iodo-5-phenylpyridine

Procedure

The 2,2-dimethyl-4(5-phenyl-2-pyridyl)-2H-1-benzopyran-6-carbonitrile used as the starting material was prepared as follows: (A) 15.98 g of 2-chloro-5-phenylpyridine were dissolved in 150 ml of 55% aqueous hydroiodic acid and the solution was heated at reflux for 2 hours. Upon cooling a solid precipitated and this was filtered off and washed with water. The solid was partitioned between diethyl ether and 2M sodium hydroxide solution, and the organic phase was dried over sodium sulphate and evaporated to give 15.87 g of 2-iodo-5-phenylpyridine which was used without further purification. (B) In an analogous manner to that described in Example 6 (A) and (B), from 2-iodo-5-phenylpyridine and 4-(1,1-dimethyl-2-propynyloxy)benzonitrile there was obtained 2,2-dimethyl-4-(5-phenyl-2-pyridyl)-2H-1-benzopyran -6-carbonitrile.

Workup

  1. customwas prepared
  2. temperaturethe solution was heated
  3. temperatureat reflux for 2 hours
  4. temperatureUpon cooling a solid
  5. customprecipitated
  6. filtrationthis was filtered off
  7. washwashed with water
  8. customThe solid was partitioned between diethyl ether and 2M sodium hydroxide solution
  9. dry with materialthe organic phase was dried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-08288dba54b64e9a813a3784b73b67a5
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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