Water → Methyl 2-amino-4-iodobenzoate

HRID 1449568Notes

Reaction equation

HRID 1449568 reaction equation
[OH-].[Na+].[I:3][C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[O:9][C:10](=O)[NH:11][C:6]=2[CH:5]=1.O>CO>[NH2:11][C:6]1[CH:5]=[C:4]([I:3])[CH:15]=[CH:14][C:7]=1[C:8]([O:9][CH3:10])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 189299207-Iodo-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 18929930Methyl 2-amino-4-iodobenzoateYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM). The mixture was heated at 60° C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed once with dilute sodium hydroxide, dried (MgSO4), filtered and concentrated to leave the title compound (2.0 g, 80%) as a brown oil which slowly crystallized; MS(CI): 278 (M+H).

Workup

  1. temperaturethe resulting solution was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed once with dilute sodium hydroxide
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f38d9f3a4bf446695c35c493e5c313e
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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