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Hydrochloric Acid → HCID 54324082, compound

HRID 1376485
Notes
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Reaction equation

HRID 1376485 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH:20]=[C:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:22]#[N:23])[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH:20]=[C:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:22]#[N:23])[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 53718435HCID 53718435, compound

Product 1

HCID 54324082HCID 54324082, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962Water
Solvent

Conditions

Temperature
50 °C

Procedure

0.5 g of 3-[1,2-dihydro-1-(3-nitrophenyl)-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile, prepared in Example 111, is suspended in 15 ml of methanol and 10 ml of water, in the presence of 0.5 g of iron powder. The suspension is heated to about 50° C. and 0.5 ml of concentrated hydrochloric acid is added dropwise. The reaction mixture is refluxed for 45 minutes and then cooled to room temperature. The residual iron is removed and the filtrate is diluted with water, treated with 0.5 g of potassium carbonate and extracted with dichloromethane. The organic phase is decanted, washed with water, dried and concentrated to give 0.2 g of 3-[1-(3-aminophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile in the form of a bright yellow solid melting at 280° C., after purification on a silica column (eluent: dichloromethane/methanol 98.5/1.5). Yield 40%.

Workup

  1. temperatureThe reaction mixture is refluxed for 45 minutes
  2. temperaturecooled to room temperature
  3. customThe residual iron is removed
  4. additionthe filtrate is diluted with water
  5. additiontreated with 0.5 g of potassium carbonate
  6. extractionextracted with dichloromethane
  7. customThe organic phase is decanted
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0708a9ff6bca454781e21b0e7a4888ca
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05663181

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes