Ammonium Chloride → HCID 10109109, compound

HRID 719199Notes

Reaction equation

HRID 719199 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([N+:26]([O-])=O)[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].[In].[Cl-].[NH4+]>C(O)C>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([NH2:26])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 10221917HCID 10221917, compound

Product 1

HCID 10109109HCID 10109109, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-nitro-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (176 mg), indium (154 mg) and saturated ammonium chloride solution (5 mL) in ethanol (20 mL) was heated to reflux for 3 hours. The reaction mixture was cooled, quenched with water and then filtered through celite. The filtrate was concentrated in vacuo, and the residue was treated with sodium bicarbonate solution, extracted into chloroform, dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a red solid (163 mg) 3-Amino-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide was prepared in an analogous manner from 3-nitro-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customquenched with water
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionthe residue was treated with sodium bicarbonate solution
  8. extractionextracted into chloroform
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7c1910753c00410fb7e42a00c381c6b0
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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