HCID 19762862, compound → HCID 67296566, compound

HRID 1189949Notes

Reaction equation

HRID 1189949 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.CC1C=CC(S(O[CH2:24][CH:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])(=O)=O)=CC=1>CCO.O>[OH:12][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:24][CH:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])[CH:3]=1)[CH2:9][C:10]#[N:11]

Participants

4

Reactant 2

HCID 19762862HCID 19762862, compoundHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Product 1

HCID 67296566HCID 67296566, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of aniline 12 (1.0 g, 6.1 mmol) in EtOH:H2O (9:1) was added 2-propylpentyl 4-methylbenzenesulfonate (0.87 g, 3.08 mmol). The reaction mixture was heated under reflux for 4 days, concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc three times. Combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to dryness. Purification by flash chromatography (25% EtOAc—hexanes) gave 3-hydroxy-3-(3-(2-propylpentylamino)phenyl)propanenitrile as a colorless semi-solid. Yield (0.3 g, 18%); 1H NMR (400 MHz, CDCl3) δ 7.17 (t, J=7.6 Hz, 1H), 6.66 (d, J=7.6 Hz, 1H), 6.62 (d, J=2.0 Hz, 1H), 6.57 (dd, J=2.0, 8.0 Hz, 1H), 4.95 (dt, J=3.2, 6.0 Hz, 1H), 3.72 (bs, 1H), 3.02 (d, J=6.0 Hz, 2H), 2.80 (d, J=6.8 Hz, 2H), 2.89 (d, J=3.2 Hz, 1H), 1.64-1.57 (m, 1H), 1.37-1.20 (m, 8H), 0.84 (t, J=6.8 Hz, 6H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 days
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc three times
  6. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure to dryness
  8. customPurification by flash chromatography (25% EtOAc—hexanes)

Sources & evidence

ORD record
ord-51f1b119d05548b68bc690914ca413f5
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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