Sodium Hydroxide → HCID 22057994, compound

HRID 967868Notes

Reaction equation

HRID 967868 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[CH3:15])([O-])=O.[OH-].[Na+]>Cl.C(O)(=O)C>[NH2:6][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[CH3:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 22057993HCID 22057993, compound

Product 1

HCID 22057994HCID 22057994, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of tin(II) chloride dihydrate (15.4 g) in concentrated hydrochloric acid (80 ml) was added to a suspension of N-(3-nitro-4-methylphenyl)-4-cyanobenzamide (6.39 g) in acetic acid (120 ml). The mixture was stirred and heated to reflux for 2 hours. The mixture was allowed to cool to ambient temperature and was basified by the addition of 2N sodium hydroxide solution. The precipitated solid was isolated and dried under vacuum at 55° C. to give N-(3-amino-4-methylphenyl)-4-cyanobenzamide (5.62 g); NMR Spectrum: (DMSOd6) 2.01 (s, 3H), 4.85 (s, 2H), 6.8 (d, 1H), 6.86 (d, 1H), 7.11 (s, 1H), 7.96 (d, 2H), 8.06 (d, 2H), 10.11 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe precipitated solid was isolated
  4. customdried under vacuum at 55° C.

Sources & evidence

ORD record
ord-e95ea4c85bf0495ebe2e62b6e347d168
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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