Sodium Hydroxide → HCID 178492068, compound

HRID 2242856Notes

Reaction equation

HRID 2242856 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:5][CH:4]=1.[OH-].[Na+]>C(Cl)Cl.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:10]([OH:20])=[C:11]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:17]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 789287N-(4-methoxyphenyl)-2-nitrobenzamide

Product 1

HCID 178492068HCID 178492068, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from step 1 (16 g, 0.059 mol), NaOH (9.4 g, 0.235 mol) and zinc (23 g, 0.352 mol) in methylene chloride (250 mL) was heated to 80° C. for 24 h. After the methanol was removed in vacuo, the aqueous residue was acidified with 10% HCl (aq.) to pH to 2. The product was collected on a filter, washed with 1N HCl, water and hexane. After dried under vacuum, the title compound (12 g, 86%) was obtained; MS (ESI+) m/z 241 (M+1, 100).

Workup

  1. customAfter the methanol was removed in vacuo
  2. customThe product was collected on a filter
  3. washwashed with 1N HCl, water and hexane
  4. customAfter dried under vacuum

Sources & evidence

ORD record
ord-ba251c516632414c9bc330e8c65b912b
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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