Water → HCID 22036991, compound

HRID 1790001Notes

Reaction equation

HRID 1790001 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH:14]=O)[CH:6]=[CH:5][CH:4]=1.Cl[C:17]1[CH:22]=[CH:21][CH:20]=C[C:18]=1[N+:23]([O-:25])=[O:24].O>CN(C=O)C>[N+:23]([C:18]1[CH:17]=[CH:22][CH:21]=[CH:20][C:14]=1[NH:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[N:3]=[CH:4][CH:5]=[CH:6]2)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 69451-Chloro-2-nitrobenzeneHCID 24758Sodium hydrideHCID 12348225N-Quinolin-8-ylformamide

Product 1

HCID 22036991HCID 22036991, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A dispersion of sodium hydride in mineral oil (0.261 mol) was added portionwise at room temperature under N2 flow to a mixture of N-8-quinolinylformamide (0.174 mol) in DMF (500 ml). The mixture was stirred at room temperature for 1 hour. A solution of 1-chloro-2-nitrobenzene (0.53 mol) in DMF (200 ml) was added dropwise. The mixture was stirred at 140° C. for 12 hours and then brought to room temperature. H2O was added and the mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (110 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 80/20; 20–45 elm). The pure fractions were collected and the solvent was evaporated, yielding 9.8 g (21%) of N-(2-nitrophenyl)-8-quinolinamine (interm. 23).

Workup

  1. stirringThe mixture was stirred at 140° C. for 12 hours
  2. custombrought to room temperature
  3. extractionthe mixture was extracted with CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue (110 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 80/20; 20–45 elm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a51d87559ef241039e7ebf5f2a91a9df
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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