N-Methoxy-N-methyl-5-nitro-3-pentafluorosulfanylbenzamide → 3-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide
Reaction equation
[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([S:14]([F:19])([F:18])([F:17])([F:16])[F:15])[CH:6]=1.[H][H]>CO.[Ni]>[NH2:11][C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:8]=1)[C:4]([N:3]([O:2][CH3:1])[CH3:21])=[O:20]Participants
5
Procedure
N-Methoxy-N-methyl-5-nitro-3-pentafluorosulfanylbenzamide (4.2 g) was dissolved in methanol (120 ml), and Raney nickel (approx. 700 mg) was added. With a hydrogen balloon attached, hydrogenation was effected on a magnetic stirrer. After 5 h, the catalyst was filtered off and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, basified with sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 1.73 g of the desired compound were obtained.
Workup
- customhydrogenation was effected on a magnetic stirrer
- filtrationthe catalyst was filtered off
- washwashed with methanol
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by means of preparative HPLC
- extractionextracted three times with ethyl acetate
- dry with materialThe combined extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8198535cd8754fee955cc4c33ffb1e51
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198272B2
Reaction notes
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