Methyl 4-aminobenzoate → Methyl 4-amino-3-iodobenzoate

HRID 1514923Notes

Reaction equation

HRID 1514923 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[I:12](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([I:12])[CH:5]=1

Participants

5

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 4104649Methyl 4-amino-3-iodobenzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-amino-benzoic acid methyl ester (1 g) in 10 mL of acetic acid and 10 mL of CH2Cl2 was added benzyltrimethylammonium dichloroiodate (2.763 g) at ambient temperature. The reaction mixture was heated at 55° C. for 1.5 h. The reaction mixture was concentrated to give the crude 4-amino-3-iodo-benzoic acid methyl ester: MS (m/z) 278.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e4de02b1bf7f4dcd936375031b15449f
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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