Chloride → 2-Chloro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid methyl ester

HRID 2235136Notes

Reaction equation

HRID 2235136 reaction equation
O.Cl(O)(=O)(=O)=O.[Cl-].[CH3:8][O:9][C:10](=[O:31])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[Cl:30]>C(O)(C)C>[CH3:8][O:9][C:10](=[O:31])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][CH2:26][NH:27]3)=[CH:22][CH:21]=2)=[O:19])=[CH:13][C:12]=1[Cl:30]

Participants

6

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 24247Perchloric AcidHCID 686984382-Chloro-4-[(quinoline-7-carbonyl)-amino]-benzoic acid methyl ester

Product 1

HCID 686967962-Chloro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid methyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Water (1.5 ml), 60% aqueous perchloric acid (0.01 ml) and pentamethylcycloopentadienyliridium(III) chloride dimer) (116 mg, 0.145 mmol, 0.05 equiv.) were added to 2-chloro-4-[(quinoline-7-carbonyl)-amino]-benzoic acid methyl ester (1.42 g, 4.17 mmol) in degassed isopropanol (100 ml) under a nitrogen atmosphere and the mixture was refluxed for 48 hours. The mixture was evaporated to give a tan solid. The solid was purified by flash chromatography (SiO2, 1:9 tert-butyl-methyl ether:dichloromethane to 1:1:8 tert-butyl-methyl ether:methanol:dichloromethane). The fractions were combined to afford 2-chloro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid methyl ester, 0.434 g (30% yield) as a tan solid. LC @215 nm; Rt 1.15: 98%, m/z (ES+): 345 (M+H+.); δH (250 MHz; d6-DMSO) 10.39 (1H, br.s), 8.07 (1H, m), 7.91-7.80 (2H, m), 7.05-6.90 (3H, m), 5.95 (1H, br.s), 3.82 (3H, s), 3.19 (2H, m), 2.70 (2H, m), 1.79 (2H, m).

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. customThe mixture was evaporated
  3. customto give a tan solid
  4. customThe solid was purified by flash chromatography (SiO2, 1:9 tert-butyl-methyl ether:dichloromethane to 1:1:8 tert-butyl-methyl ether:methanol:dichloromethane)

Sources & evidence

ORD record
ord-d975ab8e3d284ef69f5bf9059c67a1e6
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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