Methanol → Methyl 3-amino-4-iodobenzoate

HRID 1364962Notes

Reaction equation

HRID 1364962 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 118075033-Amino-4-iodobenzoic acid

Product 1

HCID 21628210Methyl 3-amino-4-iodobenzoate

Procedure

3-Amino-4-iodobenzoic acid (13.35 g, 50.8 mmol) was added to MeOH (150 mL) and SOCl2 (4.8 mL, 65.8 mmol, 1.3 equivalent) was added. The mixture was refluxed for 3 h and then volatiles were removed under reduced pressure. The residue was co-evaporated 3× with MeOH and dried in vacuo (15.23 g).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 3 h
  3. customvolatiles were removed under reduced pressure
  4. customdried in vacuo (15.23 g)

Sources & evidence

ORD record
ord-7f58fbb9f3b047d9bf16ddc8a8e0c703
Source dataset
uspto-grants-2011_02
Patent number
US07888363B2

Reaction notes

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