Methane → 2-Amino-4,5-difluorobenzoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7]C(=O)[C:5]2=[O:13].[OH:14]O.C>[OH-].[Na+]>[NH2:7][C:8]1[CH:9]=[C:10]([F:11])[C:2]([F:1])=[CH:3][C:4]=1[C:5]([OH:13])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 20 g of 5,6-difluoro-1H-indole-2,3-dione in 200 ml of 2.5N sodium hydroxide was treated dropwise with 35.7 ml of 31.4% hydrogen peroxide. The reaction mixture was warmed to 80° C. for 15 minutes, then treated with charcoal and filtered. The filtrate was cooled in an ice bath and acidified with hydrochloric acid to pH 3.5. The resulting precipitate was crystallized from xylene, giving 14.18 g of the desired compound mp 176°-178° C.
Workup
- filtrationfiltered
- temperatureThe filtrate was cooled in an ice bath
- customThe resulting precipitate was crystallized from xylene
Sources & evidence
- ORD record
- ord-268b82458ed34e3984897ecdce637ce2
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04833270
Reaction notes
Loading…