Methanol → Methyl 2-amino-4-iodobenzoate

HRID 544975Notes

Reaction equation

HRID 544975 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.O=S(Cl)Cl.[CH3:19]O>>[CH3:19][O:9][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:12]([I:14])=[CH:13][C:5]=1[NH2:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride3×HCID 14233597HCID 14233597, compound

Product 1

HCID 18929930Methyl 2-amino-4-iodobenzoate

Conditions

Temperature
65 °C

Procedure

To 2-acetylamino-4-iodo-benzoic acid (13.8 g, 45.3 mmol) in 200 mL of dry methanol was added SOCl2 (32.7 mL, 453 mmol) dropwise at 0° C. The reaction mixture was then heated at 65° C. for 2 h. The reaction was then cooled to 0° C., an additional portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65° C. for 2 h. The reaction was then cooled to 0° C., a final portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65° C. for 48 h. The reaction was then cooled to 22° C. and concentrated in vacuo. The resulting residue was diluted with H2O and extracted with 3×150 mL CH2Cl2. The combined organic fractions were washed with brine and dried over Na2SO4 to give i-b (11.7 g, 93%): MS m/z=278 (M+H).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperaturethe reaction was heated at 65° C. for 2 h
  3. temperatureThe reaction was then cooled to 0° C.
  4. temperaturethe reaction was heated at 65° C. for 48 h
  5. temperatureThe reaction was then cooled to 22° C.
  6. concentrationconcentrated in vacuo
  7. additionThe resulting residue was diluted with H2O
  8. extractionextracted with 3×150 mL CH2Cl2
  9. washThe combined organic fractions were washed with brine
  10. dry with materialdried over Na2SO4
  11. customto give i-b (11.7 g, 93%)

Sources & evidence

ORD record
ord-098383dbc3e0469b827b4e8ee428e1ec
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

Loading…