N-(2-Hydroxyethyl)ethylenediamine → HCID 22750100, compound

HRID 2164049Notes

Reaction equation

HRID 2164049 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].C(O[C:11]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[N:21]4[C:25]([C:26](=[O:27])[C:14]([C:15]=23)=[CH:13][N:12]=1)=[CH:24][CH:23]=[C:22]4[N+:28]([O-:30])=[O:29])C>CN(C)C=O>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:11]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[N:21]4[C:25]([C:26](=[O:27])[C:14]([C:15]=23)=[CH:13][N:12]=1)=[CH:24][CH:23]=[C:22]4[N+:28]([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 22750105HCID 22750105, compound

Product 1

HCID 22750100HCID 22750100, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-Hydroxyethyl)ethylenediamine (1.77 g) is added all at once to a solution, stirred and heated to 70° C., of 4-ethoxy-10-nitro-7-oxo-7H-indolizino[7,6,5-de]isoquinoline (5 g) in dimethylformamide (200 cc). The red solution thus obtained is allowed to return to ambient temperature (about 20° C.) in the course of 2 hours. A suspension of red crystals is thus obtained, to which distilled water (200 cc) is added. The crystals are filtered off and then washed with water (3 × 10 cc). After drying under reduced pressure (1 mm Hg) at 24° C., brick-red crystals of crude 4-[2-(2-hydroxyethylamino)ethylamino]-10-nitro-7-oxo-7H-indolizino[7,6,5-de]isoquinoline (5.08 g) are obtained.

Workup

  1. customThe red solution thus obtained
  2. customto return to ambient temperature
  3. custom(about 20° C.)
  4. customin the course of 2 hours
  5. additionA suspension of red crystals
  6. customis thus obtained, to which
  7. distillationdistilled water (200 cc)
  8. additionis added
  9. filtrationThe crystals are filtered off
  10. washwashed with water (3 × 10 cc)
  11. customAfter drying under reduced pressure (1 mm Hg) at 24° C.

Sources & evidence

ORD record
ord-ba5bdab6733e4a25b7071e208b0fe2fa
Source dataset
uspto-grants-1979_01
Patent number
US04137315

Reaction notes

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