Hydrochloric Acid → 3-Formyl-2-hydroxy-N-methylbenzamide

HRID 1357455Notes

Reaction equation

HRID 1357455 reaction equation
Cl.CN[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[N:12][CH3:13])[C:6]=1[OH:14].C1C[O:19]CC1>O.CC(OC)(C)C>[CH3:13][NH:12][C:11](=[O:19])[C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH:4]=[O:15])[C:6]=1[OH:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 135423458n-Methyl-3-methyliminomethyl-2-hydroxybenzamide

Product 1

HCID 113443393-Formyl-2-hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
22.5 °C

Procedure

60 ml of concentrated aqueous hydrochloric acid were added at 20 to 25° C. to 14 g (65 mmol) of the methylamide of Example 3 in a mixture of 120 ml of THF and 100 ml of water. After the reaction mixture had been stirred for approximately 14 hours at 20 to 25° C., it was taken up in MTBE and washed with water. After drying, the solvent was distilled off. 8 g of the title compound, which corresponded to 71% of theory, were obtained from the residue. (m.p.: 129-131° C.)

Workup

  1. washwashed with water
  2. customAfter drying
  3. distillationthe solvent was distilled off
  4. customwere obtained from the residue

Sources & evidence

ORD record
ord-128661d6298a412bb307d67a0eb6e58a
Source dataset
uspto-grants-2003_07
Patent number
US06593315B2

Reaction notes

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