Hydrochloric Acid → HCID 57235519, compound

HRID 1195900Notes

Reaction equation

HRID 1195900 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([C:19](=[N:21][O:22]C3CCCCO3)[CH3:20])=[C:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.Cl.[OH-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([C:19](=[N:21][OH:22])[CH3:20])=[C:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 54396025HCID 54396025, compound

Product 1

HCID 57235519HCID 57235519, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-[1-[[(tetrahydro-2H-pyran-2-yl)oxy]imino]ethyl]-1H-indole (5.0 g, 11.3 mmol) in tetrahydrofuran (115 ml) is added 10 ml of concentrated hydrochloric acid. The reaction mixture is stirred for 2-1/2 hours, at which time it is neutralized with concentrated ammonium hydroxide. It is concentrated to near dryness, diluted with ethyl acetate and washed twice with water and once with a saturated solution of sodium chloride. The organic phase is further dried over magnesium sulfate, filtered, and concentrated slowly in vacuo to 50 ml. The powdery crystals are collected to give 2.8 g (70.4%) of pure 1-(4-chlorobenzoyl)-3-[1-(hydroxyimino)ethyl]-5-methoxy-2-methyl-1H-indole; mp darkens (chars) at 170°-197° C. (dec).

Workup

  1. concentrationIt is concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed twice with water and once with a saturated solution of sodium chloride
  4. dry with materialThe organic phase is further dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated slowly in vacuo to 50 ml
  7. customThe powdery crystals are collected

Sources & evidence

ORD record
ord-3fdad259bbd643fd95abc12bed6136ed
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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