Hydrogen Bromide → HCID 178483818, compound

HRID 1267022Notes

Reaction equation

HRID 1267022 reaction equation
[CH3:1][N:2]([CH3:28])[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][N:24]=[C:25]([O:26]C)[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].Br.C([O-])(O)=O.[Na+]>CC(O)=O>[CH3:1][N:2]([CH3:28])[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][N:24]=[C:25]([OH:26])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 9842573HCID 9842573, compound

Product 1

HCID 178483818HCID 178483818, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methoxypyrido[4,3-α]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (0.056 g, 0.16 mmol) was dissolved in glacial AcOH (5 mL) and hydrobromic acid (48/50% w w; (2 mL). The mixture was refluxed for 30 min, then cooled and neutralized with solid NaHCO3. The product was extracted into CH2Cl2 (3×25 mL) dried (Na2SO4) and evaporated to give 4-hydroxypyrido[4,3-α]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (0.018 g, 33%): mp (CH2Cl2/hexane) 268-270° C. 1H NMR (CDCl3) δ 2.32 [s, 6 H, N(CH3)2], 2.61 [t, J=5.9 Hz, 2 H, CH2N(CH3)2], 3.69 (q, J=5.7 Hz, 2 H, CH2NH), 7.70 (d, J=7.1 Hz, 1 H, H-2), 7.99 (d, J=7.1 Hz, 1 H, H-1), 8.11 (d, J=9.2 Hz, 1 H, H-5),8.14 (dd, J=8.5, 7.2 Hz, 1 H, H-9), 8.46 (dd, J=8.6, 1.4 Hz, 1 H, H-8), 8.52 (d, J=9.2 Hz, 1 H, H-6), 9.98 (t, J=5.1 Hz, 1 H, CONH), 12.16 (br, 1 H, OH).

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. extractionThe product was extracted into CH2Cl2 (3×25 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0a1f5997b66543e5804bf2a60d2c7f8e
Source dataset
uspto-grants-2003_04
Patent number
US06552021B2

Reaction notes

Loading…