Hydrochloric Acid → 3-(Cyclopropylmethyl)-2,4-dihydroxy-N-methylbenzamide

HRID 893451Notes

Reaction equation

HRID 893451 reaction equation
[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8](OC)=[O:9])[CH2:3][CH2:2]1.[Cl-].[NH4+:18].Cl.[CH3:20]N>>[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8]([NH:18][CH3:20])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 25517Ammonium ChlorideHCID 15341799HCID 15341799, compound

Product 1

HCID 153418003-(Cyclopropylmethyl)-2,4-dihydroxy-N-methylbenzamide

Conditions

Temperature
50 °C

Procedure

The compound of Example 15 (112 mg) was dissolved in about 5 to 10 ml of a 40% aqueous solution of methylamine. A few crystals of ammonium chloride were added, and the reaction mixture was stirred for about 6 hours at 50° C. The reaction mixture was neutralized with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was dried, concentrated, and chromatographed on silica gel using 15% ethyl acetate/85% hexane as eluant to give the product.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customchromatographed on silica gel using 15% ethyl acetate/85% hexane as eluant
  5. customto give the product

Sources & evidence

ORD record
ord-c65b8ed832b146c58c8ed544c7f0db39
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

Loading…