Ethylenediamine → Pixantrone

HRID 1720236Notes

Reaction equation

HRID 1720236 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].F[C:6]1[C:11]2[C:12](=[O:21])[C:13]3[CH:14]=[CH:15][N:16]=[CH:17][C:18]=3[C:19](=[O:20])[C:10]=2[C:9](F)=[CH:8][CH:7]=1>C1COCC1>[NH2:3][CH2:2][CH2:1][NH:4][C:6]1[C:11]2[C:12](=[O:21])[C:13]3[CH:14]=[CH:15][N:16]=[CH:17][C:18]=3[C:19](=[O:20])[C:10]=2[C:9]([NH:3][CH2:2][CH2:1][NH2:4])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 101059046,9-Difluorobenzo[g]isoquinoline-5,10-dione

Product 1

HCID 134019Pixantrone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution (55° C.) of ethylenediamine (154.4 mL, 2.29 mol) in THF (1400 mL), 6,9-difluorobenzo[g]isoquinoline-5,10-dione (70.1 g, 0.29 mol) was portionwise added over a period of 2.5 hours (about 4.6 g/10' each portion). The mixture was stirred for 3 hours at the same temperature and a blue precipitate was gradually formed. After one night stirring at 25° C., the suspension was filtered under nitrogen blanket, washed with THF (200 mL) and dried under vacuum (15 torr, 60° C., 3 h) to yield crude 6,9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione as dihydrofluoride salt (117 g).

Workup

  1. customa blue precipitate was gradually formed
  2. stirringAfter one night stirring at 25° C.
  3. filtrationthe suspension was filtered under nitrogen blanket
  4. washwashed with THF (200 mL)
  5. customdried under vacuum (15 torr, 60° C., 3 h)

Sources & evidence

ORD record
ord-58e601bed5a04b1f8a6ece98e8d895b0
Source dataset
uspto-grants-1996_04
Patent number
US05506232

Reaction notes

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