HCID 2310517, compound → HCID 28722141, compound

HRID 362901Notes

Reaction equation

HRID 362901 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:14]([CH:15]([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:18]([CH3:20])[CH3:19])=[O:7])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:10]([CH:18]([CH3:19])[CH3:20])=[CH:11][CH:12]=[CH:13][C:14]=1[CH:15]([CH3:16])[CH3:17])=[O:7]

Participants

4

Reactant 1

HCID 2310517HCID 2310517, compound

Product 1

HCID 28722141HCID 28722141, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Step 2): Zinc powder (7.81 g, 119 mmol) was added slowly to a solution of 2-nitro-N-(2,6-diisopropylphenyl)benzamide (2.0 g, 6.3 mmol) in acetic acid (38.3 ml) below 10° C. The mixture was stirred for 2 hours at room temperature. The excess reagent was filtered off and the filtrate was neutralized with 10% NaOH solution. The mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated. The residue was recrystallized (ethyl acetate/hexane) to give 2-amino-N-(2,6-diisopropylphenyl)benzamide (77.1%): mp 207°-209° C.

Workup

  1. filtrationThe excess reagent was filtered off
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-63f074694e314d39b0587e3303bb8a86
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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