Hydrochloric Acid → N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamide

HRID 1586202

Reaction equation

HRID 1586202 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]N)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[C:19]1(=[O:35])[N:23]([CH2:24][CH2:25][CH2:26][C:27](=O)[CH3:28])[C:22](=[O:30])[C:21]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:20]12.Cl.CCCCCC>C(O)C>[CH3:28][C:27]1[NH:15][C:12]2[C:13]([C:26]=1[CH2:25][CH2:24][N:23]1[C:22](=[O:30])[C:21]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:20]3[C:19]1=[O:35])=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:10][CH:11]=2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8058HexaneHCID 2362702-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dioneHCID 118316844-(4-Fluorobenzoyl)aminophenylhydrazine

Product 1

HCID 23290476N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamideYield 6.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5.33 gm (21.7 mMol) 4-(4-fluorobenzoyl)aminophenylhydrazine and 5.03 gm (21.8 mMol) 5-phthalimidyl-2-pentanone in 100 mL ethanol were added 2 mL concentrated hydrochloric acid and the reaction mixture was heated at 80° C. for 14 hours. To the reaction mixture were then added an additional 3 mL concentrated hydrochloric acid and heating continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and 100 mL hexane were slowly added. The solid which formed was filtered and washed with hexane and provided, after drying, 6.67 gm of the desired compound. The mother liquor was concentrated under reduced pressure and then subjected to silica gel chromatography, eluting with 1:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide an additional 0.63 gm of product. Overall yield was 7.3 gm (76%).

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customThe solid which formed
  4. filtrationwas filtered
  5. washwashed with hexane
  6. customprovided
  7. customafter drying
  8. concentrationThe mother liquor was concentrated under reduced pressure
  9. washeluting with 1:1 hexane
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-819c94266a2841929f7934dcc8ce59c6
Source dataset
uspto-grants-1999_08
Patent number
US05942536

Linked notes

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