Hydrochloric Acid → N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

HRID 1461445Notes

Reaction equation

HRID 1461445 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][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]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[N-:25]=[C:26]=[O:27].[Na+].Cl>O1CCOCC1.O.C(OCC)(=O)C>[NH2:25][C:26]([N:20]([OH:21])[CH2:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:8]([C:6](=[O:7])[C:5]2[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[CH3:22])=[O:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11051568NaNCOHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 15027396N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamineYield 53.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine (500 mg, 1.45 mmol) in 30 ml of 1,4-dioxane and 15 ml of water at 0° C. is added sodium isocyanate (104 mg, 1.59 mmol) followed by 1.59 ml (1.59 mmol) of 1N hydrochloric acid. The reaction mixture is diluted with ethyl acetate and washed once with water, and finally with a saturated solution of sodium chloride. It is further dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue is recrystallized from methylene chloride and dried to give 300 mg (53%) of pure N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole -3-methanamine (535); mp 151.5°-154° C. dec.

Workup

  1. washwashed once with water
  2. dry with materialIt is further dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is recrystallized from methylene chloride
  6. customdried

Sources & evidence

ORD record
ord-d266b5b1acd94d54b40a1ece8cf64daf
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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