Water → HCID 9869398, compound

HRID 497440Notes

Reaction equation

HRID 497440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:5][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:16][C:17]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:18]=3[C:19]([O:21]C)=[O:20])[CH:13]=2)[CH2:8]1.[OH-].[Na+].O>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:5][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:16][C:17]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:18]=3[C:19]([OH:21])=[O:20])[CH:13]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22319323HCID 22319323, compound

Product 1

HCID 9869398HCID 9869398, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The methyl benzoate (0.65 g) was dissolved in 10 mL 1:1 THF/MeOH, and this solution was treated with 2 mL 50% NaOH and 1 mL water and stirred at room temperature for 18 hours. When the starting material was no longer observed by mass spec, the mixture was concentrated, the solids were dissolved in ethyl acetate/water 1:1. The layers were separated, and the aqueous layer was extracted with 2×20 mL ethyl acetate. The organic layers were combined and washed with 10 mL 50% saturated NaCl, dried over MgSO4/Na2SO4, filtered, and concentrated. The residual oil was purified by column chromatography (MPLC, silica, gradient 98:2 to 80:20)(CH2Cl2/MeOH+1% NH4OH). Fractions containing the desired product were combined, concentrated, and dried in vacuo overnight to give 2-[2-(3,4-dichlorobenzylamino)-indan-5-ylamino]-5-nitro-benzoic acid (0.38 g, 60% yield). MS (APCI) m/z 470.0 (M+−1). CHN for (C23H19Cl2N3O4·CH2Cl2) calc: C, 55.58, H, 3.94, N, 8.31; found: C, 55.25, H, 3.88, N, 8.32.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe solids were dissolved in ethyl acetate/water 1:1
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 2×20 mL ethyl acetate
  5. washwashed with 10 mL 50% saturated NaCl
  6. dry with materialdried over MgSO4/Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residual oil was purified by column chromatography (MPLC, silica, gradient 98:2 to 80:20)(CH2Cl2/MeOH+1% NH4OH)
  10. additionFractions containing the desired product
  11. concentrationconcentrated
  12. customdried in vacuo overnight

Sources & evidence

ORD record
ord-0b13c0ab05444153a5af43ce2019876f
Source dataset
uspto-grants-2005_09
Patent number
US06949575B2

Reaction notes

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