Water → HCID 178520828, compound

HRID 1076712Notes

Reaction equation

HRID 1076712 reaction equation
[C:1]1([C:7]2([OH:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][CH2:20][CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[OH:22][CH2:21][CH2:20][CH2:19][NH:18][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 90863-Amino-1-propanolHCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-one

Product 1

HCID 178520828HCID 178520828, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-Phenyl-3-hydroxy-3H-indol-2-one (4.5 g.) was heated under reflux with 3-aminopropanol (6.0 g.) in xylene (100 ml.) and toluene-p-sulphonic acid (150 mg) in an apparatus fitted with a water separator. After 24 hours the reaction mixture was cooled. The product crystallised and was filtered off and recrystallised from methanol to give the title compound, 3.81 g., m.p. 215°-217°C. (Found C, 72.4; H, 6.7; N. 9.9, C17H18N2O2 requires C, 72.3; H, 6.4; N, 9.9%).

Workup

  1. temperatureAfter 24 hours the reaction mixture was cooled
  2. customThe product crystallised
  3. filtrationwas filtered off
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-564097dba93443b88aeeb8643f51b32a
Source dataset
uspto-grants-1976_05
Patent number
US03957819

Reaction notes

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