Sodium Dithionite → 4-fluoro-2-methyl-1H-indol-5-ol

HRID 407265Notes

Reaction equation

HRID 407265 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[CH2:12][C:13](=O)[CH3:14].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(=O)([O-])[O-].[K+].[K+].O>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:12]=[C:13]([CH3:14])[NH:9]2

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 223379951-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

Product 1

HCID 103520364-fluoro-2-methyl-1H-indol-5-olYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (1 g) was dissolved in a solution of potassium carbonate (1.3 g) in water (13 ml). A solution of sodium dithionite (5.24 g) in water (12.3 ml) was added dropwise. The mixture was stirred for 1.5 hours, then left to stand overnight. The solid was filtered and washed with water (6 ml). The solid was dried at 35° C. in a vacuum oven to give crude 4-fluoro-2-methyl-1H-indol-5-ol (0.5 g, 64.5%).

Workup

  1. waitleft
  2. waitto stand overnight
  3. filtrationThe solid was filtered
  4. washwashed with water (6 ml)
  5. customThe solid was dried at 35° C. in a vacuum oven

Sources & evidence

ORD record
ord-44ce491d415445f3aa87e17d1af8167b
Source dataset
uspto-grants-2014_06
Patent number
US08754240B2

Reaction notes

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