Pyridine → HCID 20571559, compound

HRID 1577058Notes

Reaction equation

HRID 1577058 reaction equation
C([C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][CH2:11][CH3:12])#N.[N:14]1C=CC=C[CH:15]=1.[Br:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:24](Cl)=[O:25]>CCOCC>[C:15]([C:4]1[CH:3]=[C:8]([CH2:9][CH2:10][CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[O:13][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[C:21]([Br:20])[CH:22]=1)#[N:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13548200HCID 13548200, compoundHCID 20530897HCID 20530897, compound

Product 1

HCID 20571559HCID 20571559, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4.2 g (0.024 mol) of the 3-cyano-4-n-butylphenol prepared in Step V was dissolved in 50 ml ether, and 6 ml pyridine was added as a catalyst. 9.7 g (0.029 mol) of the 3-bromo-4-n-heptyloxybenzoyl chloride solution prepared in Step III and 30 ml of ether was slowly added to the reaction solution with violently shaking in a water bath having floating ice cubes. After the addition, the reaction solution was allowed to stand at room temperature for a while and was refluxed for two hours. After completion of the reaction, the reaction mixture was filtered to remove inorganic salt. An organic layer was cleaned and dehydrated and the solvent was distilled off. The residue was recrystallized in hexane to yield 9.9 g of (2'-cyano-4'-n-butylphenyl)-3-bromo-4-n-heptyloxybenzoate. The calculated yield was 87.6%.

Workup

  1. additionAfter the addition
  2. customto stand at room temperature for a while
  3. temperaturewas refluxed for two hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction mixture was filtered
  6. customto remove inorganic salt
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized in hexane

Sources & evidence

ORD record
ord-055adf69695f4f63a1520cd19ef74c42
Source dataset
uspto-grants-1981_09
Patent number
US04287085

Reaction notes

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