Hydrochloric Acid → HCID 14459487, compound

HRID 1031465Notes

Reaction equation

HRID 1031465 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([C:23]2[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].[ClH:37]>O.[Cu]Cl>[Cl:37][C:6]1[CH:7]=[C:8]([C:23]2[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 14459482HCID 14459482, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14459487HCID 14459487, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

An ice cold solution of 0.9 g (8.5 mmol) of sodium nitrite in 5 ml of water is added dropwise over a period of 10 minutes to a solution of 3.0 g (8.3 mmol) of 6-[3-amino-4-(4-ethoxycarbonylpiperazin-1-yl)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone in 7 ml of conc. hydrochloric acid and 3 ml of water at -5° C. The resulting reaction mixture is then added to a solution of 1.29 g (13 mmol) of copper-(I) chloride in 5 ml of conc. hydrochloric acid which is at 0° C. When evolution of gas has ceased, the solution is slowly heated to 50° C. and then cooled and adjusted to pH 11 with potassium carbonate. The aqueous phase is extracted three times with 50 ml of dichloromethane and the organic phases are dried, filtered and concentrated by evaporation under vacuum. The residue obtained is chromatographed on silica gel with dichloromethane/methanol (95:5) and after concentration of the lipophilic main fraction under vacuum it yields 1.2 g (38%) of a colourless solid, m.p. 154°-156° C.

Workup

  1. customThe resulting reaction mixture
  2. customis at 0° C
  3. temperaturecooled
  4. extractionThe aqueous phase is extracted three times with 50 ml of dichloromethane
  5. customthe organic phases are dried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under vacuum
  8. customThe residue obtained
  9. customis chromatographed on silica gel with dichloromethane/methanol (95:5)

Sources & evidence

ORD record
ord-d831633b855b498d816aef5b60cdb047
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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