Hydrochloric Acid → HCID 59500510, compound

HRID 452052Notes

Reaction equation

HRID 452052 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[N+:22]([O-])=O)([O-])=O.[BH4-].[Na+].Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[NH2:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59500462HCID 59500462, compound

Product 1

HCID 59500510HCID 59500510, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

16.6 g (42 mmol) of 3′,2″-dinitro-p-quaterphenyl and 1.99 g of Pd/C (10%) are suspended in 200 ml of methanol, and 8.4 g (222 mmol) of sodium borohydride are added in portions with stirring at 0° C. After stirring for 2 hours, the clear solution is neutralised with dilute HCl. The solvent is then removed, and the residue is washed intensively with water and recrystallised from dioxane. The precipitate is filtered and dried in vacuo, giving 11 g (35.6 mmol) of a crystalline solid. The overall yield is 78%.

Workup

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

Sources & evidence

ORD record
ord-2f043423019c4712bd6091fcc99b913f
Source dataset
uspto-grants-2013_07
Patent number
US08487300B2

Reaction notes

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