Hydrochloric Acid → HCID 54151577, compound

HRID 597042Notes

Reaction equation

HRID 597042 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH:6]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl[C:20]1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]=[C:22]([CH3:32])[CH:21]=1.Cl.C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:20]1[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:23]=[C:22]([CH3:32])[CH:21]=1)[CH:7]([CH3:12])[CH:6]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 5982554-Chloro-6-methyl-2-phenylpyrimidineHCID 21449390HCID 21449390, compound

Product 1

HCID 54151577HCID 54151577, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-methoxy-2-methylindolin-3-ylacetate (2.0g.), 6-chloro-4-methyl-2-phenylpyrimidine (1.76g.) and concentrated hydrochloric acid (0.5ml.) in ethanol (50ml.) was heated under reflux for 5 hours. The solution was cooled, saturated sodium acetate solution (3ml.) was added, and the mixture was concentrated in vacuo. The residue was diluted with water (30ml.) and extracted with ethyl acetate (3 × 30ml.). The combined exracts were washed with water and then dried (Na2SO4), and the solvent was evaporated in vacuo at ca 50° C. to give ethyl 5-methoxy-2-methyl-1-(4-methyl-2-phenylpyrimidin-6-yl)indolin-3-ylacetate as a syrup. This was shown to be pure by TLC (System A) and by NMR spectroscopy (OCH3 at 6.23τ).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution was cooled
  4. concentrationthe mixture was concentrated in vacuo
  5. additionThe residue was diluted with water (30ml.)
  6. extractionextracted with ethyl acetate (3 × 30ml.)
  7. washThe combined exracts were washed with water
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was evaporated in vacuo at ca 50° C.

Sources & evidence

ORD record
ord-8e284d2e7c944bc7a104a073324b5994
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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