Water → 2-((3-Chlorophenyl)carbonyl)amino-5-nitroindane

HRID 1637178Notes

Reaction equation

HRID 1637178 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27].O>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([C:26]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=3)[CH2:4]2)=[O:27])[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 223193245-Nitro-indan-2-ylamine hydrochloride

Product 1

HCID 232983992-((3-Chlorophenyl)carbonyl)amino-5-nitroindane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-amino-5-nitroindane hydrochloride (1.5 g, 7.0 mmol) in methylene chloride (50 ml) at 0° C. was added triethylamine (2.1 ml, 15.0 mmol) follwed by 3-chlorobenzoyl chloride (1.0 ml, 7.5 mmol). The mixture was dumped immediately into water and the layers separated. The aqueous layer was extracted with methylene chloride (2×20 ml) and the combined extracts washed with water, dried over MgSO4, filtered, and concentrated to an oil which was homogeneous by TLC and used immediately in the next step: M.S. (M+H)+ =317.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with methylene chloride (2×20 ml)
  3. washthe combined extracts washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil which

Sources & evidence

ORD record
ord-888b99650a6845a6aafaa25f2b3c65e1
Source dataset
uspto-grants-2000_03
Patent number
US06040314

Reaction notes

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