Hydrochloric Acid → 1-benzoyl-5-chloromethyl-2,3-dihydro-1H-indole

HRID 426634Notes

Reaction equation

HRID 426634 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.Cl.[C:21](Cl)(Cl)(Cl)[Cl:22].CCCCCC>C(O)(=O)C>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:21][Cl:22])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6812141-benzoyl-2,3-dihydro-1H-indoleHCID 21584008Carbon tetrachloride hexane

Product 1

HCID 130214281-benzoyl-5-chloromethyl-2,3-dihydro-1H-indoleYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Benzoyl-2,3-dihydro-1H-indole (Beilstein, 20, 257) (5.58 g, 25 mmole) is dissolved in 50 ml of glacial acetic acid, then 56 ml (ca 70 mmoles) of 40% formaldehyde are added, and dry hydrogen chloride passed into the solution which is maintained at 70° for 3 hours. The solution is evaporated, and the residue dissolved in benzene, and again evaporated to dryness to give 6.53 g of crude product. This residue is treated with carbon tetrachloride-hexane to give 4.05 g (60%) of 1-benzoyl-5-chloromethyl-2,3-dihydro-1H-indole, m.p. 107.5°-110.0°.

Workup

  1. temperatureis maintained at 70° for 3 hours
  2. customThe solution is evaporated
  3. dissolutionthe residue dissolved in benzene
  4. customagain evaporated to dryness
  5. customto give 6.53 g of crude product

Sources & evidence

ORD record
ord-c81e0b60b03346a98b096a5e2c775af9
Source dataset
uspto-grants-1979_10
Patent number
US04170654

Reaction notes

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