Hydrochloric Acid → Benzoic acid, 4-amino-3-hydroxy-, methyl ester

HRID 1421720Notes

Reaction equation

HRID 1421720 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].Cl.[CH3:13]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Procedure

Through a solution of 4-amino-3-hydroxybenzoic acid (75 g, 0.49 mol) in 2.0 L of dry CH3OH at room temperature was bubbled anhydrous HCl gas until the solution was saturated. The solution was stirred for 48 hr, then concentrated in vacuo. The product was partitioned between EtOAc and saturated aq. NaHCO3 solution, and the organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the title. 1H NMR (CDCl3, 400 MHz): d 7.51 (dd, 1H, J=8.1 and 1.9 Hz, ArH); 7.46 (d, 1H, J=1.9 Hz, ArH); 6.66 (d, 1H, J=8.1 Hz, ArH); 5.31 (bs, 1H, OH); 4.13 (bs, 2H, NH2) and 3.85 (s, 3H, OCH3).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was partitioned between EtOAc and saturated aq. NaHCO3 solution
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto provide the title

Sources & evidence

ORD record
ord-8b0d02d8688d40a7917914c25086e281
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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