HCID 21093457, compound → HCID 135797752, compound

HRID 1350519Notes

Reaction equation

HRID 1350519 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[C:4]([N+:17]([O-])=O)[CH:3]=1>C(O)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]([NH2:12])=[N:17][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 21093457HCID 21093457, compound

Product 1

HCID 135797752HCID 135797752, compoundYield 144.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Combine 2-(4-chloro-2-nitro-phenylamino)-benzonitrile (1.2 g, 4.4 mmol) in ethanol (40 mL) with a solution of stannous chloride dihydrate (2.9 g, 13.2 mmol) in 12 N hydrochloric acid (13 mL). Stir and reflux for 2 hours, cool to ambient temperature and concentrate. Add water (200 mL), filter and dry to give (890 mg, 72%) of the title compound as a yellow solid: 1H NMR (DMSO-d6) δ 6.84–6.69 (m, 5E), 7.27–7.17 (m, 2H), 8.02 (s, 1H), 8.83 (bs, 1H), 9.36 (bs, 1H); MS (APCI) m/z (rel intensity) 244.3 (100).

Workup

  1. temperaturereflux for 2 hours
  2. concentrationconcentrate
  3. filtrationAdd water (200 mL), filter
  4. customdry

Sources & evidence

ORD record
ord-8298394c91614919a6d69c240f5b5170
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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