HCID 13533635, compound → HCID 9862708, compound

HRID 464507Notes

Reaction equation

HRID 464507 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](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:5]([C:24]#[N:25])=[CH:4][N:3]=1>C(O)(=O)C.[Ni]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:24][N:25]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:9]3[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=3[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 13533635HCID 13533635, compound

Product 1

HCID 9862708HCID 9862708, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 50 mg (0.142 mmole) of the end product of Example 10 in 10 ml of acetic acid was treated with 1/4 spatula of Raney nickel, and hydrogenated for 2.5 hrs. The reaction was filtered through celite, evaporated, and partitioned between 30 ml of dichloromethane and 15 ml of dilute ammonium hydroxide. The organic layer was dried with sodium sulfate, evaporated and the residue was refluxed in ethanol for 1 hr, and then evaporated to dryness. The solid was dissolved in dichloromethane and developed on a thick layer silica gel plate in ethyl acetate/ethanol (20/1). The band of Rf 0.3 was removed and crystallized from ether to give white prisms, mp 243°-248° C., and a mixed mp of 244°-248° C. with authentic material obtained as in Example 2.

Workup

  1. filtrationThe reaction was filtered through celite
  2. customevaporated
  3. custompartitioned between 30 ml of dichloromethane and 15 ml of dilute ammonium hydroxide
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customevaporated
  6. temperaturethe residue was refluxed in ethanol for 1 hr
  7. customevaporated to dryness
  8. dissolutionThe solid was dissolved in dichloromethane
  9. customThe band of Rf 0.3 was removed
  10. customcrystallized from ether
  11. customto give white prisms, mp 243°-248° C.
  12. customa mixed mp of 244°-248° C. with authentic material obtained as in Example 2

Sources & evidence

ORD record
ord-77c0af30a4874567a9f9230c5488600f
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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