Methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate → HCID 22024119, compound

HRID 1792891Notes

Reaction equation

HRID 1792891 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[NH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

3

Reactant 1

HCID 22024122Methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate

Product 1

HCID 22024119HCID 22024119, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 8.00 g (25.3 mmol) of methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate is admixed with 3.2 g of palladium on activated carbon (5%) and hydrogenated at room temperature and under atmospheric pressure for 6 h. The reaction mixture is then filtered, the filtrate is concentrated to dryness and the residue is purified by silica gel chromatography [TLC (SiO2)ethyl acetate/n-heptane 1:1; Rf=0.38] using ethyl acetate/n-heptane (1:1). Evaporation gives 6.23 g (86% of theory) of methyl 2-amino-6-[(tert-butylamino)sulfonyl]benzoate as a beige solid of melting point 132-133° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. customthe residue is purified by silica gel chromatography [TLC (SiO2)ethyl acetate/n-heptane 1:1; Rf=0.38]
  4. customEvaporation

Sources & evidence

ORD record
ord-e109df869bcb46d5a4484519939d7541
Source dataset
uspto-grants-2006_07
Patent number
US07078369B2

Reaction notes

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