HCID 14209955, compound → HCID 14209962, compound

HRID 1196887Notes

Reaction equation

HRID 1196887 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([NH2:15])=[C:9]([N+:12]([O-])=O)[CH:10]=2)[C:5](=[O:16])[NH:4][CH2:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:17])[C:11]2[CH:10]=[C:9]3[NH:12][C:10]([C:11]4[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=4)=[N:15][C:8]3=[CH:7][C:6]=2[C:5](=[O:16])[NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 14209955HCID 14209955, compound

Product 1

HCID 14209962HCID 14209962, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5 g. (20.4 mmole) 4,4-dimethyl-6-nitro-7-amino-1,2,3,4-tetrahydroisoquinolin-1-one were hydrogenated in 120 ml. methanol in the presence of 0.5 g. 10% palladium on charcoal. After separating off the catalyst, the evaporation residue (4.3 g.) was acylated in 150 ml. methylene chloride and 8.4 ml. triethylamine with 5.4 g. isonicotinic acid chloride hydrochloride. After 1 hour, the evaporation residue is worked up with water and filtered off with suction. The moist residue was subsequently boiled in 100 ml. ethanol and 20 ml. concentrated hydrochloric acid for 24 hours, evaporated, mixed with water and neutralized. After column chromatography (silica gel, elution agent: methylene chloride/methanol saturated with ammonia; 15:1 v/v) and boiling up, there were obtained 2.3 g. (41% of theory) of the title compound; m.p. above 300° C.

Workup

  1. customAfter separating off the catalyst
  2. filtrationfiltered off with suction
  3. waitconcentrated hydrochloric acid for 24 hours
  4. customevaporated
  5. additionmixed with water
  6. washAfter column chromatography (silica gel, elution agent: methylene chloride/methanol saturated with ammonia; 15:1 v/v)
  7. customthere were obtained 2.3 g

Sources & evidence

ORD record
ord-f99f0478061049a28a1e55a06117c009
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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