HCID 53766268, compound → HCID 22902288, compound

HRID 1489781Notes

Reaction equation

HRID 1489781 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1>[NH:1]1[C:23]2[C:11](=[CH:12][C:13]3[CH2:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:21]=3[CH:22]=2)[CH:10]=[C:4]1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 53766268HCID 53766268, compound

Product 1

HCID 22902288HCID 22902288, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-azido-3-fluoren-2-ylacrylate suspended in dry toluene was heated at reflux for 1 h, and the resulting solution was then evaporated to dryness in vacuo. The resulting mixture of ethyl 1,5-dihydroindino[2,1-f]indole-2-carboxylate and ethyl 1,10-dihydroindino[1,2-g]-indole-2-carboxylate was crystallised from ethanol, thus removing most of the [1,2 g] isomer and leaving the title compound (contained with approximately 30% of the [1,2-g]isomer) in the mother liquors which were evaporated to dryness. δH (CDCl3) 9.11 (1H, s, br, 1-NH), 7.82-7.76 (3H, m), 7.56-7.52 (1H, m), 7.37 (H, dd, J 1 and 7), 7.34-7.28 (1H, m), 7.25 (1H, dd, J 1 and 2), 4.45 (2H, q, OCH2CH3), 3.97 (2H, s, CH2) and 1.46 (3H, t, OCH2CH3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customthe resulting solution was then evaporated to dryness in vacuo
  4. additionThe resulting mixture of ethyl 1,5-dihydroindino[2,1-f]indole-2-carboxylate and ethyl 1,10-dihydroindino[1,2-g]-indole-2-carboxylate
  5. customwas crystallised from ethanol
  6. customthus removing most of the [1,2 g] isomer

Sources & evidence

ORD record
ord-7f999e8d4903488e91fc896a2c2fa91f
Source dataset
uspto-grants-1997_10
Patent number
US05679694

Reaction notes

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