Pyridine → HCID 20392245, compound

HRID 1863169Notes

Reaction equation

HRID 1863169 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12]3=[CH:14][S:15][CH:16]=[C:11]3[C:10](=[O:17])[NH:9][C:8]=2[CH:18]=1)([O-])=O.N1C=CC=CC=1>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12]3=[CH:14][S:15][CH:16]=[C:11]3[C:10](=[O:17])[NH:9][C:8]=2[CH:18]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 20392248HCID 20392248, compound

Product 1

HCID 20392245HCID 20392245, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 7.8 g. portion of 4,9-dihydro-7-nitro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in a mixture of 200 ml. of pyridine and 50 ml. of methanol with 200 mg. of 10% palladium on carbon catalyst was shaken for 2 hours in a Parr hydrogenator. The catalyst was filtered and the solvents were removed under vacuum on the steam bath. The residue was dissolved in dilute hydrochloric acid, filtered, and the filtrate was made alkaline with sodium hydroxide. The crystals which form are recovered by filtration and air dried given the desired product as a brown powder, m.p. 212°-215° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvents were removed under vacuum on the steam bath
  3. dissolutionThe residue was dissolved in dilute hydrochloric acid
  4. filtrationfiltered
  5. customThe crystals which form
  6. filtrationare recovered by filtration and air
  7. customdried

Sources & evidence

ORD record
ord-08a35eb7a4ce4988ade283bf89760d71
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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