Triethylamine → 2-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester

HRID 1392259

Reaction equation

HRID 1392259 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[NH2:6].C(N(CC)CC)C.[C:22]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=1[NH:6][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 596476Methyl 4-nitroanthranilate

Product 1

HCID 691945292-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-nitro-anthranilic acid methyl ester (5.060 g, 25.8 mmol) in CH2Cl2 (200 mL) was added triethylamine (8 mL) and 4-tert-butyl benzoyl chloride and the reaction was stirred overnight at rt. It was then poured into brine, extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester (1.841 g, 86%) as a yellow solid. mp=146.0-148.4° C.; mass spectrum (−ES, M−H) m/z 355. 1H NMR (400 MHz, DMSO-d6); δ 11.60 (bs, 1H), 9.35 (d, 1H), 8.20 (d, 1H), 8.02 (dd, 1H), 7.90 (d, 2H), 7.64 (d, 2H), 3.95 (s, 3H), 1.36 (s, 9H). Elemental analysis: Calcd. for C19H20N2O5: C, 64.04; H, 5.66; N, 7.86. Found: C, 64.04; H, 5.79; N, 7.76.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2c456c3544ae41e4900a48bcbda31214
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Linked notes

Loading…