Water → 2-chloro-1H-indole

HRID 2043660Notes

Reaction equation

HRID 2043660 reaction equation
O=P(Cl)(Cl)[Cl:3].C([N:8]([CH2:15][CH3:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.N1C2C(=CC=CC=2)CC1=O.O>C1(C)C=CC=CC=1>[Cl:3][C:15]1[NH:8][C:9]2[C:10]([CH:16]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

6

Reactant 4

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 321710Oxindole

Product 1

HCID 6408402-chloro-1H-indoleYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, POCl3 (1 ml, 10.82 mmol, 2 eq) is added to a well stirred suspension of N,N-diethylaniline (1 ml, 5.41 mmol, 1 eq) and 1,3-dihydro-2H-indol-2-one x159 (0.72 g, 5.41 mmol, 1 eq) in dry toluene (15 ml). The mixture is heated at reflux during 3 hours. After cooling, water (15 ml) is carefully added and the organic layer is washed with water (3×25 ml). The organic layer is dried on anhydrous MgSO4, filtered off and concentrated under reduced pressure to obtain 0.76 g of 2-chloro-1H-indole x160 as an orange solid (0.76 g, 93%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux during 3 hours
  3. temperatureAfter cooling
  4. washthe organic layer is washed with water (3×25 ml)
  5. dry with materialThe organic layer is dried on anhydrous MgSO4
  6. filtrationfiltered off
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6717535aea564e34bf848f4962cc9eee
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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