Hydrogen Peroxide → HCID 59375146, compound

HRID 1811124Notes

Reaction equation

HRID 1811124 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16](C=O)=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1.OO.S(=O)(=O)(O)[OH:29].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([OH:29])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 86642953HCID 86642953, compound

Product 1

HCID 59375146HCID 59375146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 2 A solution of crude 4-(2-fluorophenyl)-7-formyl-9H-carbazole-1-carboxamide (25.2 mg, 0.076 mmol) in methanol (2 mL) at 0° C. was treated with 30% aqueous hydrogen peroxide (0.039 mL, 0.379 mmol) and sulfuric acid (0.020 mL, 0.379 mmol). After 1.5 h, additional hydrogen peroxide (0.100 mL) and sulfuric acid (0.050 mL) were added and the mixture was stirred at rt overnight. After 16 h, 1 M aqueous sodium hydroxide (2 mL) was added and the mixture was stirred for 1 h. The pH was adjusted to ca. 4 and the organic solvent was removed under vacuum. The aqueous residue was diluted with water and the precipitate was collected by filtration, washed with water and dried. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide as tan solid after lypholization (5.1 mg, 21%). 1H NMR (400 MHz, methanol-d4) δ 7.81 (1H, d, J=7.70 Hz), 7.45-7.64 (2 H, m), 7.21-7.42 (2 H, m), 7.03 (1 H, d, J=7.92 Hz), 6.90-6.99 (2 H, m), 6.45 (1 H, dd, J=8.58, 2.20 Hz). Mass spectrum m/z 321.0 (M+H)+.

Workup

  1. waitAfter 16 h
  2. stirringthe mixture was stirred for 1 h
  3. customthe organic solvent was removed under vacuum
  4. additionThe aqueous residue was diluted with water
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-32e0c2a7881842b2b15992aa1ae46d6d
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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