9-Chloro-6H-indolo[2,3-b]quinoxaline → HCID 20071536, compound

HRID 981050Notes

Reaction equation

HRID 981050 reaction equation
[Na].Cl.[CH3:3][N:4]([CH2:6][CH2:7][Cl:8])[CH3:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]2[NH:16][C:17]3[C:26]([C:12]=2[CH:11]=1)=[N:25][C:24]1[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[N:18]=3>COCCO>[ClH:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]2[N:16]([CH2:7][CH2:6][N:4]([CH3:3])[CH3:5])[C:17]3[C:26]([C:12]=2[CH:11]=1)=[N:25][C:24]1[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[N:18]=3

Participants

5

Reactant 3

HCID 52938709-Chloro-6H-indolo[2,3-b]quinoxalineHCID 5360545SodiumHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 20071536HCID 20071536, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

5.06 g sodium (0.22 mole) is dissolved in 300 ml 2-methoxyethanol, 15.9 g N,N-dimethylamino-2-chloroethane-HCl (0.11 mole) is added followed by 25.4 g 9-chloro-6H-indolo(2,3-b)quinoxaline (0.10 mole). The mixture is heated for 3 hours at 100° C., cooled and filtered. The filtrate is concentrated and poured into water. The raw base obtained is filtered off and washed with water and subjected to chromatography on silica gel with methanol as eluent. The purified base is dissolved after drying in acetone. The hydrochloride is precipitated by slowly dropwise adding concentrated hydrochloric acid with stirring. Yield 23.2 g, 66%, mp. 243°-246° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. additionpoured into water

Sources & evidence

ORD record
ord-1b2ad66461f24e86b081e58d7959bd32
Source dataset
uspto-grants-1991_02
Patent number
US04990510

Reaction notes

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