Sodium hydride → HCID 21093457, compound

HRID 1350518Notes

Reaction equation

HRID 1350518 reaction equation
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[H-].[Na+].Br[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>C1COCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]#[N:9])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 729132-AminobenzonitrileHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 21093457HCID 21093457, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine anthranilonitrile (2.36 g, 20 mmol), sodium hydride (1.2 g (60% in oil), 30 mmol) and THF (50 mL), stir at ambient temperature for 30 minutes. Add 1-bromo4-chloro-2-nitro-benzene (7.1 g, 30 mmol) and stir at ambient temperature for 3 days. Pour the reaction mixture in ice-cold concentrated hydrochloric acid (200 mL) and filter the resulting solid. Purify by flash chromatography (dichloromethane) and recrystallize from hot ethyl acetate to give (1.62 g, 30%) of the title compound as orange needles: 1H NMR (CDCl3) δ 7.17 (d, 1H), 7.26 (t, 1H), 7.40–7.51 (m, 2H), 7.61 (t, 1H), 7.72 (d, 1H), 8.22 (d, 1H), 9.54 (bs, 1H).

Workup

  1. filtrationfilter the resulting solid
  2. customPurify by flash chromatography (dichloromethane)
  3. customrecrystallize from hot ethyl acetate

Sources & evidence

ORD record
ord-c362cd8c9a904b698276bbef125162b2
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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