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

HRID 2263467Notes

Reaction equation

HRID 2263467 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-7c86d454f4064188902972944c5df30b
Source dataset
uspto-grants-2010_12
Patent number
US07851623B2

Reaction notes

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