Hydrochloric Acid → HCID 67106154, compound

HRID 1907066Notes

Reaction equation

HRID 1907066 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]1[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=1)[CH:10]=[CH:9]2)([O-])=O.[BH4-].[Na+].Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]1[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=1)[CH:10]=[CH:9]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67106258HCID 67106258, compound

Product 1

HCID 67106154HCID 67106154, compoundYield 135.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

12.6 g (42 mmol) of 8-nitro-2-naphthylquinoline and 1.99 g of Pd/C (10%) are suspended in 200 ml of methanol. 8.4 g (222 mmol) of sodium borohydride are added in portions with stirring at 0° C. After stirring for 2 h, the clear solution is neutralised using dilute HCl. The solvent is then removed, and the resultant residue is washed vigorously with water and recrystallised from dioxane. The precipitate is filtered and dried in vacuo, giving 9.9 g (56.9 mmol) of crystalline solid. The overall yield is 88%.

Workup

  1. stirringAfter stirring for 2 h
  2. customThe solvent is then removed
  3. washthe resultant residue is washed vigorously with water
  4. customrecrystallised from dioxane
  5. filtrationThe precipitate is filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-07110f227e0846ceb5ccfe957153c8c7
Source dataset
uspto-grants-2013_12
Patent number
US08597798B2

Reaction notes

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