p-Toluenesulfonic acid → HCID 178520830, compound

HRID 1076709Notes

Reaction equation

HRID 1076709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=O)[CH:5]=[CH:6][CH:7]=1.C1(C)C(C)=CC=CC=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[NH:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 90863-Amino-1-propanolHCID 21490326HCID 21490326, compound

Product 1

HCID 178520830HCID 178520830, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(m-Chlorophenyl)-3-hydroxy-3H-indol-2-one (25.9 g., U.K. specification No. 1,125,671), xylene (400 ml.), 3-aminopropanol (15 g.) and toluene-p-sulphonic acid (150 mg.) were heated under reflux, with stirring, in an apparatus fitted with a water separator. After 24 hours, 6.9 ml. of water and 3-aminopropanol had been collected. The mixture was cooled and the xylene removed under reduced pressure leaving a yellow crystalline material which was recrystallised from ethyl acetate to give the title compound (14.33 g.), m.p. 164° to 165°C. (Found C, 64.45; H, 5.4; N, 8.85. C17H17Cl2N2O2 requires C, 64.75; H, 5.6; N, 8.7%).

Workup

  1. temperatureunder reflux
  2. customof water and 3-aminopropanol had been collected
  3. temperatureThe mixture was cooled
  4. customthe xylene removed under reduced pressure
  5. customleaving a yellow crystalline material which
  6. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-837694bdb95f4d6fa584ad260ee2c0fc
Source dataset
uspto-grants-1976_05
Patent number
US03957819

Reaction notes

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