Methanol → HCID 13388223, compound

HRID 895015Notes

Reaction equation

HRID 895015 reaction equation
FC(F)(F)C(N)=O.[Cl:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12.[OH-].[Na+].CO>O>[Cl:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:29])[NH2:27])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86737970HCID 86737970, compound

Product 1

HCID 13388223HCID 13388223, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g (1.1 mmole) of 6-chloro-7,8-methylenedioxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide, 0.1 g of sodium hydroxide and 50 ml of methanol was stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The combined extracts were washed with brine, dried and concentrated. The residue was chromatographed on 20 g of silica gel with a gradient of 1% to 5% of methanol in chloroform to give 0.35 g of pure 6-chloro-7,8-methylenedioxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine. This was suspended in 5 ml of dry methylene chloride, cooled to -60° C. and a solution of 5 ml of boron tribromide in methylene chloride (1 g/ml) was added dropwise with stirring under a nitrogen atmosphere. The mixture was stirred for about an hour at room temperature, recooled to -15° when excess methanol was added cautiously. The solvents were evaporated. The residue was azeotroped several times with methanol. The remaining solid was crystallized from methanol-acetonitrile ether to give 0.36 g (86%) of 6-chloro-7,8-dihydroxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. 289°-290°.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 20 g of silica gel with a gradient of 1% to 5% of methanol in chloroform

Sources & evidence

ORD record
ord-2feee3270ebe453397581750bf2d3883
Source dataset
uspto-grants-1981_08
Patent number
US04285938

Reaction notes

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