Hydrochloric Acid → HCID 21938287, compound

HRID 1242148Notes

Reaction equation

HRID 1242148 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[NH:7][C:6]=1[CH3:18].C(O)C.[OH-].[Na+].Cl>O>[C:14]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:18])=[C:5]2[CH2:4][C:3]1[CH:19]=[CH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:22][C:2]=1[Cl:1])([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21938261HCID 21938261, compound

Product 1

HCID 21938287HCID 21938287, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-(2-chloro-4-phenylbenzyl)-5-methoxycarbonyl-2-methylindole (0.95 g), added are ethanol (5 ml), water (5 ml) and aqueous sodium hydroxide (0.29 g), and refluxed for 3 hours. The reaction mixture is cooled, and neutralized with HCl. This is extracted with ethyl acetate and water, and the organic layer is dried and concentrated. The resulting residue is crystallized from a small amount of a mixed solution of chloroform and ether. The crystal is taken out through filtration and dried to obtain 5-carboxy-3-(2-chloro-4-phenylbenzyl)-2-methylindole (145) (0.701 g)

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionThis is extracted with ethyl acetate and water
  4. customthe organic layer is dried
  5. concentrationconcentrated
  6. customThe resulting residue is crystallized from a small amount of a mixed solution of chloroform and ether
  7. filtrationThe crystal is taken out through filtration
  8. customdried

Sources & evidence

ORD record
ord-e490ebf46d4f491d9955b78b52e718ac
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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