Hydrochloric Acid → HCID 11807538, compound

HRID 1267004Notes

Reaction equation

HRID 1267004 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]3[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([O:15]C)=[O:14])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N1C2C(=C(NC3C([N+]([O-])=O)=CC=CC=3C(O)=O)C=CC=2)C=N1.[BH4-].[Na+].Cl>[OH-].[Na+].CC(O)=O>[CH:3]1[C:4]2=[C:5]3[C:6](=[CH:7][CH:8]=[C:9]2[NH:1][N:2]=1)[N:21]=[C:20]1[C:11]([C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=[CH:19]1)=[N:10]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 11045183HCID 11045183, compoundHCID 11781490HCID 11781490, compound

Product 1

HCID 11807538HCID 11807538, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-(1H-indazol-4-ylamino)-3-nitrobenzoate (254 mg, 0.85 mmol) in 2 M NaOH (20 mL) was stirred at room temperature for 1 h to complete hydrolysis to 2-(1H-indazol-4-ylamino)-3-nitrobenzoic acid then NaBH4 (194 mg, 5.11 mmol) was added and the mixture heated under reflux for 30 min. The mixture was then acidified with conc. HCl, then glacial AcOH, until the pH reached 5. This aqueous solution was then extracted with EtOAc (3×50 mL), the extracts combined and dried (Na2SO4), and the solvent removed under reduced pressure. Crystallization from acetone gave 3H-pyrazolo[4,3-a]phenazine-10-carboxylic acid (97 mg, 43%); mp 305-310° C.; 1H NMR [(CD3)2SO] δ 7.98 (br s, 1 H, H-4), 8.07 (dd, J=8.6, 7.2 Hz, 1 H, H-8), 8.20 (d, J=9.2 Hz, 1 H, H-5), 8.53 (dd, J=8.5, 1.3 Hz, 1 H, H-7 or H-9), 8.60 (dd, J=7.1, 1.3 Hz, 1 H, H-9 or H-7), 8.90 (v br s, 1 H, H-1), 14.26 (v br s, 1 H, NH or COOH), 14.76 (v br s, 1 H, NH or COOH).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 min
  3. extractionThis aqueous solution was then extracted with EtOAc (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customCrystallization from acetone

Sources & evidence

ORD record
ord-5a1d8c00527e4d8d975066c8bc7a2779
Source dataset
uspto-grants-2003_04
Patent number
US06552021B2

Reaction notes

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