2-Chloro-5-nitrobenzoic acid → HCID 3727890, compound

HRID 1898865Notes

Reaction equation

HRID 1898865 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[OH:26].C([O-])(=O)C.[Na+]>O1CCOCC1.O>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]2[O:26][C:20]3[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:19]=3[NH:18][C:4](=[O:6])[C:3]=2[CH:7]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 172872-Chloro-5-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 760822-Amino-5-methylphenolHCID 517045Sodium Acetate

Product 1

HCID 3727890HCID 3727890, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 20.2 g (0.1 mole) of 2-chloro-5-nitrobenzoic acid and 8.4 ml thionyl chloride in 100 ml of dioxane was refluxed for 90 minutes. The solution was cooled to 50° C. and added to a suspension of 12.3 g (0.1 mole) of 2-amino-5-methyl phenol in 50 ml of water. After about half of the acid chloride was added, 8.2 g sodium acetate was added, then the rest of the acid chloride was added dropwise. The reaction mixture was stirred for 45 minutes at 50° C. Ice water was added to the mixture with stirring, and the resulting precipitate was filtered and washed with water. The filter cake was dissolved in 150 ml of water containing 4 g of NaOH and stirred for 1 hour at 85°-95° C., then cooled to room temperature. The cooled solution was acidified with HCl, filtered, and washed with water. The precipitate was dried to yield 11.3 g (42%) of 2-nitro-7-methyldibenz[b,f][1,4]oxazepin-11(10H)-one, mp 264°-266° C.

Workup

  1. temperaturewas refluxed for 90 minutes
  2. stirringwith stirring
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. dissolutionThe filter cake was dissolved in 150 ml of water containing 4 g of NaOH
  6. stirringstirred for 1 hour at 85°-95° C.
  7. temperaturecooled to room temperature
  8. filtrationfiltered
  9. washwashed with water
  10. customThe precipitate was dried

Sources & evidence

ORD record
ord-8d920793a75340738bb4c332cc95947f
Source dataset
uspto-grants-1996_11
Patent number
US05571806

Reaction notes

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