Potassium Hydroxide → HCID 20295993, compound

HRID 1389940Notes

Reaction equation

HRID 1389940 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])[C:14](N)=[O:15].[OH-:25].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])[C:14]([OH:25])=[O:15]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20295996HCID 20295996, compound

Product 1

HCID 20295993HCID 20295993, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.6 parts of 2-methoxy-α-[(2-methylphenyl)amino]-1-naphthaleneacetamide and 120 parts of a solution of potassium hydroxide in ethanol 1 N is stirred and refluxed for 64 hours. The reaction mixture is evaporated and the residue is taken up in 250 parts of water. The unreacted starting material "A" is filtered off and the filtrate is neutralized with glacial acetic acid. The precipitated product is filtered off and dissolved in 140 parts of 1,1'-oxybisethane. The solution is washed with 100 parts of water, dried, filtered and evaporated. The solid residue is crystallized from 40 parts of 2-propanol at 0° C. The product is filtered off and dried, yielding 4.8 parts (35.5%) of 2-methoxy-α-[(2-methylphenyl)amino]-1-naphthaleneacetic acid; mp. 187.5° C.

Workup

  1. temperaturerefluxed for 64 hours
  2. customThe reaction mixture is evaporated
  3. filtrationThe unreacted starting material "A" is filtered off
  4. filtrationThe precipitated product is filtered off
  5. dissolutiondissolved in 140 parts of 1,1'-oxybisethane
  6. washThe solution is washed with 100 parts of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid residue is crystallized from 40 parts of 2-propanol at 0° C
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-9aa7994a855b4beda29bbdff734af145
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

Loading…