Hydrochloric Acid → HCID 18174496, compound

HRID 395702Notes

Reaction equation

HRID 395702 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][Si](C(C)(C)C)(C)C)=[CH:12][C:11]=2[N:24]2[C:32](=[O:33])[C:31]3[CH:30]=[C:29]4[CH:34]=[CH:35][CH:36]=[CH:37][C:28]4=[CH:27][C:26]=3[C:25]2=[O:38])=[O:8])=[CH:5][CH:4]=1.O1CCOCC1.Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[N:24]2[C:25](=[O:38])[C:26]3[CH:27]=[C:28]4[CH:37]=[CH:36][CH:35]=[CH:34][C:29]4=[CH:30][C:31]=3[C:32]2=[O:33])=[O:8])=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 18174557HCID 18174557, compound

Product 1

HCID 18174496HCID 18174496, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-methoxybenzoyl)-2-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)-4-(tert-butyldimethylsiloxy)benzeneamine (48.6 mg, 0.088 mmol) in 2:1 dioxane:methanol (6 mL) was treated with 12 M aqueous hydrochloric acid (0.010 mL). After 6 h, the mixture was concentrated in vacuo and the residue purified by flash chromatography (silica gel; ethyl acetate/hexanes) to yield 24.6 mg (64%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f57393359b8d41f6b0a43ad16a29074f
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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