Tetrahydrofuran → 3-Fluoro-2-methyl-6-nitroaniline

HRID 2233164Notes

Reaction equation

HRID 2233164 reaction equation
ClCC([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([F:15])[C:7]=1[CH3:16])=O.[OH-].[Na+].O1CCCC1>O>[F:15][C:8]1[C:7]([CH3:16])=[C:6]([C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1)[NH2:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 675482572-chloro-N-(3-fluoro-2-methyl-6-nitrophenyl)acetamide

Product 1

HCID 38312103-Fluoro-2-methyl-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-N-(3-fluoro-2-methyl-6-nitrophenyl)acetamide (prepared from 47.2 g of 2-chloro-N-(3-fluoro-2-methylphenyl)acetamide, ca. 234 mmol) was suspended in water (220 ml) then treated with aqueous sodium hydroxide solution (12.5M, 110 ml, 1.37 mol). Tetrahydrofuran (110 ml) was added, then the mixture was heated to reflux for 5 hours, then evaporated (removing most of the tetrahydrofuran). The yellow solid was filtered off and washed with water until washing were non-alkaline. Drying in vacuo afforded a yellow solid (32.3 g, 81% over 2 steps) containing ˜13% isomer.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. customevaporated (
  4. customremoving most of the tetrahydrofuran)
  5. filtrationThe yellow solid was filtered off
  6. washwashed with water
  7. washuntil washing
  8. customDrying in vacuo
  9. customafforded a yellow solid (32.3 g, 81% over 2 steps)
  10. additioncontaining ˜13% isomer

Sources & evidence

ORD record
ord-fd03afd31c0541f1b48f5bd777a05cd4
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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