Phenylacetone → 7-Chloro-1,2-dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

HRID 267234Notes

Reaction equation

HRID 267234 reaction equation
N[N:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:12]1([CH2:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]3=[C:9]([C:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:19]([CH3:20])[N:2]3[CH2:3][CH2:4]2)[CH:8]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 517045Sodium AcetateHCID 203105795-Chloro-n-aminoindoline

Product 1

HCID 215559787-Chloro-1,2-dihydro-4-methyl-5-phenylpyrrolo[3,2,1-hi]indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 13 g. (0.077 mole) of 1-amino-5-chloroindoline, 10 g. (0.073 mole) of phenylacetone and 10 g. of sodium acetate in 120 ml. of glacial acetic acid was heated on a steam bath for 1 hour. The mixture was cooled, filtered and the solid material washed with acetic acid and water. The product was recrystallized from benzene-isooctane; yield 12.7 g. (65%); m.p. 202°-204°C.).

Workup

  1. additionA mixture of 13 g
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid material washed with acetic acid and water
  5. customThe product was recrystallized from benzene-isooctane

Sources & evidence

ORD record
ord-a84fba1b055041828ca419e557721f3d
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

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