Sodium Dithionite → 4-(7-Hydroxybenzo[e][1,2,4]triazin-3-yl)benzoic acid

HRID 1472693Notes

Reaction equation

HRID 1472693 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N+:12]([O-])[C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C.O>[OH:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=3)[N:11]=[N:12][C:13]=2[CH:19]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 178524233HCID 178524233, compound

Product 1

HCID 1360984144-(7-Hydroxybenzo[e][1,2,4]triazin-3-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(4-Carboxyphenyl)-7-hydroxybenzo[e][1,2,4]triazine 1-oxide (Compound VII-1, 350 mg, 1.23 mmol) was dissolved in 70% ethanol in water (20 ml) at reflux. 5.0 equivalents of Na2S2O4 were added. The reaction turned dark brown. After 30 minutes, the solution was concentrated to remove ethanol and the solid was filtered and washed with water and dried (12 mg). 1H NMR (DMSO-d6 400 MHz): δ 8.67 (d, 2H), 8.16 (d, 2H), 8.09 (d, 1H), 7.77 (d, 1H), 7.67 (s, 1H). MS (ESI): m/z 268.43 [M+1]+.

Workup

  1. temperatureat reflux
  2. concentrationthe solution was concentrated
  3. customto remove ethanol
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried (12 mg)

Sources & evidence

ORD record
ord-309279c52a7f48f08a5ef4fe6543c602
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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