HCID 13533634, compound → HCID 13533635, compound

HRID 464161Notes

Reaction equation

HRID 464161 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[C:15]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])OC(CCl)C[O:16]2)[C:5]([C:29]#[N:30])=[CH:4][N:3]=1>CO.Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[C:15](=[O:16])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[C:5]([C:29]#[N:30])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 13533634HCID 13533634, compound

Product 1

HCID 13533635HCID 13533635, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 0.2 g (0.448 mmole) of the end product of Example 9 in 20 ml of methanol and 10 ml of 3N hydrochloric acid was refluxed for 20 mins and the solvent was evaporated. The residue was partitioned between 50 ml of dichloromethane and 30 ml of dilute ammonium hydroxide, and the organic layer was dried, concentrated and filtered through 15 g of Florisil. The column was eluted with 200 ml of ether which was concentrated, filtered and recrystallized from dichloromethane/ether/petrol to give white prisms, mp 153°-157° C.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between 50 ml of dichloromethane and 30 ml of dilute ammonium hydroxide
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. filtrationfiltered through 15 g of Florisil
  6. washThe column was eluted with 200 ml of ether which
  7. concentrationwas concentrated
  8. filtrationfiltered
  9. customrecrystallized from dichloromethane/ether/petrol
  10. customto give white prisms, mp 153°-157° C.

Sources & evidence

ORD record
ord-a1a6c4567a1d4d8ca95e4dd2caa60175
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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