2-Amino-6-chlorobenzoic acid → HCID 68865411, compound

HRID 1725996Notes

Reaction equation

HRID 1725996 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[CH3:12][Si](C=[N+]=[N-])(C)C.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27]>C1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH:11][S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[F:19])(=[O:28])=[O:27])[C:7]=1[C:8]([O:10][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 750712-Amino-6-chlorobenzoic acidHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 68865411HCID 68865411, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A solution of 6-chloroanthranilic acid (1.9549 g, 11.57 mmol) in 4:1 benzene/methanol (58 mL) was treated with trimethylsilyldiazomethane (7.0 mL, 14.0 mmol, 2.0M solution in hexanes), stirred for 18 hours, quenched with acetic acid (1 mL), and concentrated. The concentrate (2.04 g, 10.99 mmol) was dissolved in pyridine (22 mL), treated with 2-fluorobenzenesulfonyl chloride (1.75 mL, 13.19 mmol), stirred for 18 hours, quenched with 1N HCl (200 mL), and treated with ethyl acetate (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography (3:1 hexanes/ethyl acetate) to provide the desired product (2.50 g, 66%). MS (ESI(+)) m/e 361 (M+H)+, 366 (M+NH4)+; MS (ESI(−)) m/e 342 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.52 (br s, 1H), 7.72 (m, 2H), 7.43 (m, 3H), 7.37 (td, 1H), 7.22 (dd, 1H), 3.68 (s, 3H).

Workup

  1. customquenched with acetic acid (1 mL)
  2. concentrationconcentrated
  3. concentrationThe concentrate (2.04 g, 10.99 mmol)
  4. dissolutionwas dissolved in pyridine (22 mL)
  5. stirringstirred for 18 hours
  6. customquenched with 1N HCl (200 mL)
  7. additiontreated with ethyl acetate (100 mL)
  8. washThe organic layer was washed with brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe concentrate was purified by flash column chromatography (3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a6881c55fc4d451bbc483ed547958e66
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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