Hydrochloric Acid → HCID 21938236, compound

HRID 2187754Notes

Reaction equation

HRID 2187754 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][CH:11]=[C:10]([C:16]([O:18]C)=[O:17])[CH:9]=2)=O.O.NN.[OH-].[K+].Cl>C(O)CO.O>[C:16]([C:10]1[CH:9]=[C:8]2[C:13]([C:14]([CH3:15])=[C:6]([CH2:4][C:3]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:2]=3[Cl:1])[NH:7]2)=[CH:12][CH:11]=1)([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21938274HCID 21938274, compound

Product 1

HCID 21938236HCID 21938236, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

2-(2,4-Dichlorobenzoyl)-6-(methoxycarbonyl)-3-methylindole (1.00 g) is suspended in ethylene glycol (10 ml), to which is added hydrazine monohydrate (0.83 g), and stirred under heat at 160° C. for 3 hours. After this is once cooled, potassium hydroxide (1.1 g) is added thereto, and again stirred under heat at 155° C. for 3 hours. After cooled, the reaction mixture is made acidic with water and 1 M HCl added thereto. Then, this is extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried with anhydrous sodium sulfate. Then, the drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting crystalline residue is washed with a mixed solution of ethyl acetate and hexane, and dried to obtain 6-carboxy-2-(2,4-dichlorobenzyl)-3-methylindole (86) (0.63 g).

Workup

  1. temperatureAfter this is once cooled
  2. stirringagain stirred
  3. temperatureunder heat at 155° C. for 3 hours
  4. temperatureAfter cooled
  5. additionadded
  6. extractionThen, this is extracted with ethyl acetate
  7. washThe organic layer is washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThen, the drying agent is removed through filtration
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. washThe resulting crystalline residue is washed with a mixed solution of ethyl acetate and hexane
  12. customdried

Sources & evidence

ORD record
ord-ec04ed4a1b1a4a12ae4aeb0b5f4593a8
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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