Isatin → Tryptanthrine

HRID 399177Notes

Reaction equation

HRID 399177 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([O:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=[O:11])=O.[NH:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)C(=O)[C:14]1=O>N1C=CC=CC=1>[CH:20]1[CH:21]=[CH:22][C:23]2[N:13]=[C:14]3[N:12]([C:4]4[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=4[C:7]3=[O:9])[C:10](=[O:11])[C:18]=2[CH:19]=1

Participants

4

Reactant 2

HCID 7054IsatinHCID 8359Isatoic Anhydride

Product 1

HCID 73549TryptanthrineYield 38.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11 g (0.068 mol) of the isato acid anhydride of the aforesaid formula (1a-1), and 10 g (0.068 mol) of isatine represented by the following formula: ##STR75## and 20 ml of pyridine were heated under reflux for 6 hours in a 200 ml eggplant type flask to be reacted. After the reaction solution was cooled, a crystal precipitated in the reaction solution was filtered off to give 6.46 g (yield: 38%) of tryptanthrine represented by the following formula. ##STR76##

Workup

  1. temperatureunder reflux for 6 hours in a 200 ml eggplant type flask
  2. customto be reacted
  3. temperatureAfter the reaction solution was cooled
  4. customa crystal precipitated in the reaction solution
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-dac9f06756774ac4b6b04ad5182e4dd6
Source dataset
uspto-grants-1998_10
Patent number
US05817810

Reaction notes

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