Hydrazine hydrate (1:1) → 1-amino-1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one

HRID 344818Notes

Reaction equation

HRID 344818 reaction equation
C1(C=[N:8][CH:9]2[C:17]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]3=[O:26])[CH2:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)C=CC=CC=1.O.NN>C(O)C>[NH2:8][CH:9]1[C:17]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:26])[CH2:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21477837HCID 21477837, compound

Product 1

HCID 149942711-amino-1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry consisting of 1,3-dihydro-1-[(phenylmethylene)amino]-spiro[2H-indene-2,3'-[3H]indole]-2'(1'H)one (13.8 g), and absolute ethanol (300 ml) was added hydrazine hydrate (13.9 ml). The resulting mixture was heated at reflux for 3 hours, cooled to room temperature and the resulting precipitate removed by filtration. The mother liquor was concentrated and the resulting oil solidified upon addition of ethyl acetate-hexane. The resulting solid was recovered by filtration. Additional product was obtained from the mother liquor as above. Recrystallization from ethyl acetate afforded 1-amino-1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one, m.p. 195°-197° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe resulting precipitate removed by filtration
  4. concentrationThe mother liquor was concentrated
  5. additionthe resulting oil solidified upon addition of ethyl acetate-hexane
  6. filtrationThe resulting solid was recovered by filtration
  7. customAdditional product was obtained from the mother liquor as above
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8818ef8f0ad1496a8afe6a28ccb47b8e
Source dataset
uspto-grants-1991_10
Patent number
US05053511

Reaction notes

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