Phenol → HCID 59596279, compound

HRID 2264716Notes

Reaction equation

HRID 2264716 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[N:17])#[N:9].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CC[O:26]CC>>[NH2:9][C:8]1[C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]([C:20]2[CH:19]=[CH:18][C:23]([OH:26])=[CH:22][CH:21]=2)([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)[N:17]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 3283Diethyl EtherHCID 7042PhthalonitrileHCID 8058Hexane

Product 1

HCID 59596279HCID 59596279, compoundYield 20%

Conditions

Temperature
185 °C

Procedure

A mixture of phenol (294 g, 3.10 moles) and 1,2-dicyanobenzene (20 g, 0.16 moles) was heated to reflux at 185° C. for 3 hours. The reaction was cooled to room temperature and diluted with 2:1 ether:hexane (1.5 L). The resulting precipitate was stirred for 1 hour and filtered. The isolated filter cake was triturated with dichloromethane (0.6 L), stirred for 0.5 hour and filtered. The crude compound was purified using flash chromatography (silica; 65:30:5 dichloromethane:acetone: methanol with 0.1% NH4OH, 8 L; 50:50 dichloromethane:methanol with 0.1% NH4OH, 4 L; methanol with 0.1% NH4OH, 1 L) to give the title compound as a pale yellow solid (9 g, 20%). 1H NMR (300 MHz, DMSO-d6/TFA-d) δ 8.47 (d, J=7.8 Hz, 1 H), 7.91 (t, J=7.2 Hz, 1 H), 7.87 (m, 2 H), 7.25 (d, J=8.7 Hz, 4 H), 6.98 (d, J=8.7 Hz, 4 H); MS (ES+) m/z 317 [M+1]+; tR=1.24 min.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. filtrationThe isolated filter cake
  5. customwas triturated with dichloromethane (0.6 L)
  6. stirringstirred for 0.5 hour
  7. filtrationfiltered
  8. customThe crude compound was purified

Sources & evidence

ORD record
ord-af1df3dea5bc44a78f4d7ac9166f4bcd
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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