Sodium Hydroxide → HCID 10113310, compound

HRID 497439Notes

Reaction equation

HRID 497439 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[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][CH:24]=[CH:23][C:18]=3[C:19]([O:21]C)=[O:20])[CH:13]=2)[CH2:8]1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[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][CH:24]=[CH:23][C:18]=3[C:19]([OH:21])=[O:20])[CH:13]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10114199HCID 10114199, compound

Product 1

HCID 10113310HCID 10113310, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-[2-(3,4-dichloro-benzylamino)-indan-5-ylamino]-benzoate (0.98 g) was dissolved in 20 mL 1:1 THF/MeOH, and this solution was treated with 9 mL 50% NaOH and stirred at room temperature for 24 hours. When the starting material was no longer observed by mass spec, the mixture was concentrated to remove the MeOH, extracted with diethyl ether, and the precipitate was collected by filtration and dried in vacuo overnight to give 2-[2-(3,4-dichlorobenzylamino)-indane-5-ylamino]-benzoic acid (0.09 g, 10% yield). MS (APCI) m/z 427.1 (M++1). CHN for (C23H20Cl2N2O2.1.85HCl) calc: C, 55.83, H, 4.45, N, 5.66; found: C, 55.45, H, 4.22, N, 5.50.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the MeOH
  3. extractionextracted with diethyl ether
  4. filtrationthe precipitate was collected by filtration
  5. customdried in vacuo overnight

Sources & evidence

ORD record
ord-ae00bf66cd2d4a8b93518c5e3a4f1934
Source dataset
uspto-grants-2005_09
Patent number
US06949575B2

Reaction notes

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