2,6-Dichloro-4-nitroaniline → HCID 23036551, compound

HRID 1709697Notes

Reaction equation

HRID 1709697 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([Cl:17])[C:8]=1[NH2:9].CO[CH:20]1[CH:28]2[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[CH:22](OC)O1.C(OCC)(=O)C>C(O)(=O)C.O>[Cl:6][C:7]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([Cl:17])[C:8]=1[N:9]1[CH:20]=[C:28]2[C:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:22]1

Participants

7

Reactant 4

HCID 74302,6-Dichloro-4-nitroanilineHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 12295473HCID 12295473, compound

Product 1

HCID 23036551HCID 23036551, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of sodium acetate (14.0 g) in 225 ml of acetic acid heated to refluxing is first added 2,6-dichloro-4-nitroaniline (6.40 g, 30.8 mmol), followed by 1,3-dimethoxyoctahydroisobenzofuran (5.73 g, 30.8 mmol). The reaction mixture is heated under reflux for 16 hours, after which the acetic acid is stripped off by rotoevaporation and the residue is poured into ethyl acetate and water. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are washed with water and with brine and dried. The residue is purified by column chromatography to give 2-(2,6-dichloro-4-nitrophenyl)-4,5,6,7-tetrahydroisoindole, which is then reduced with stannous chloride according to Example 9 procedures to give 3,5-dichloro-4-(4,5,6,7-tetrahydroisoindol-2-yl)aniline.

Workup

  1. temperatureheated
  2. temperatureto refluxing
  3. temperatureThe reaction mixture is heated
  4. temperatureunder reflux for 16 hours
  5. extractionThe aqueous layer is extracted with ethyl acetate
  6. washthe combined organic layers are washed with water and with brine
  7. customdried
  8. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-a0a1aca5e0c841769d8764f0ec11a1c7
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Reaction notes

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