Hydrochloric Acid → Methyl 2,4-dimethoxy-5-methylaminobenzoate

HRID 2293549Notes

Reaction equation

HRID 2293549 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([NH:15][CH:16]=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].CO.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([NH:15][CH3:16])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21476992Methyl 5-formamido-2,4-dimethoxybenzoate

Product 1

HCID 21477068Methyl 2,4-dimethoxy-5-methylaminobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 1.60 g portion of methyl 2,4-dimethoxy-5-formylaminobenzoate was dissolved in 20 ml of tetrahydrofuran, and 1.7 ml of borane dimethylsulfide complex was added under ice-cooling, followed by 2 hours of stirring at 60° C. Then, 3 ml of methanol and 4 ml of concentrated hydrochloric acid were added, followed by stirring at 75° C. for a while and then spontaneously cooled. The thus precipitated product of interest was collected by filtration, washed with tetrahydrofuran and then dried under a reduced pressure to give 1.08 g of methyl 2,4-dimethoxy-5-methylaminobenzoate.

Workup

  1. addition1.7 ml of borane dimethylsulfide complex was added under ice-
  2. temperaturecooling
  3. stirringby stirring at 75° C. for a while
  4. temperaturespontaneously cooled
  5. filtrationThe thus precipitated product of interest was collected by filtration
  6. washwashed with tetrahydrofuran
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-f6544039bc6f4e6bbbeb65aac2fcf2c4
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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