Ammonium Chloride → HCID 19372781, compound

HRID 129229Notes

Reaction equation

HRID 129229 reaction equation
[C:1]([NH:4][CH:5]1[CH2:34][C:9]2=[CH:10][N:11]([S:16]([C:19]3[C:24]([CH:25]([CH3:27])[CH3:26])=[CH:23][C:22]([CH:28]([CH3:30])[CH3:29])=[CH:21][C:20]=3[CH:31]([CH3:33])[CH3:32])(=[O:18])=[O:17])[C:12]3[CH:13]=[CH:14][CH:15]=[C:7]([C:8]=32)[C:6]1=[O:35])(=[O:3])[CH3:2].[CH3:36][Mg]Br.[NH4+].[Cl-]>C1COCC1>[C:1]([NH:4][CH:5]1[CH2:34][C:9]2=[CH:10][N:11]([S:16]([C:19]3[C:20]([CH:31]([CH3:33])[CH3:32])=[CH:21][C:22]([CH:28]([CH3:29])[CH3:30])=[CH:23][C:24]=3[CH:25]([CH3:26])[CH3:27])(=[O:18])=[O:17])[C:12]3[CH:13]=[CH:14][CH:15]=[C:7]([C:8]=32)[C:6]1([OH:35])[CH3:36])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19028832HCID 19028832, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19372781HCID 19372781, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-acetylamino-3,4-dihydro-1-(2,4,6-triisopropylphenylsulfonyl)-benz[cd]indol-5-one (3.57 g, 7.0 mmol) in THF (70 ml) was added, at 40° C. in argon streams, a solution of 1M methyl magnesium bromide in THF (8 equivalents relative to ketone compound). The mixture was warmed to room temperature, and stirred for 4 hours. The reaction mixture was added to an ice-cooled saturated aqueous solution of NH4Cl and the mixture was subjected to extraction with ethyl acetate. The extract was washed with an aqueous saline solution and, then, dried (anhydrous Na2SO4). The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with n-hexane-ethyl acetate (1:2) to afford 1.27 g (36%) of the title compound as an amorphous crystalline product. 1H-NMR(CDCl3, 200MHz) δ: 1.09(d,J=7 Hz,12H), 1.25(d,J=7 Hz,6H), 1.95(s,3H), 2.7-3.0(m,2H), 3.24(dd,J=16, 5 Hz,1H), 4.14(hept,J=7 Hz,2H), 4.54(m,1H), 5.3-5.5(br,1H), 7.1-7.4(m,6H) ppm. IR(KBr):3390, 2965, 1660 cm-1. Anal: Calcd for C29H38N2O4S.H2O: C 65.88%, H 7.63%, N 5.30% Found; C 66.13%, H 7.28%, N 5.69%.

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washThe extract was washed with an aqueous saline solution
  3. dry with materialdried (anhydrous Na2SO4)
  4. distillationThe solvent was distilled off under reduced pressure
  5. washeluting with n-hexane-ethyl acetate (1:2)

Sources & evidence

ORD record
ord-02c5b468b87841ea89e49797faa52f08
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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