Methyl iodide → Methyl 4-(acetylamino)-3-nitrobenzoate

HRID 2400187Notes

Reaction equation

HRID 2400187 reaction equation
[C:1]([NH:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1O)(=[O:3])[CH3:2].[CH:18](N(C(C)C)CC)(C)C.CI>CN(C=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:18])=[O:10])=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 33646654-(Acetylamino)-3-hydroxy-5-nitrobenzoic acid

Product 1

HCID 236856Methyl 4-(acetylamino)-3-nitrobenzoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 107 (1.50 g, 6.69 mmol) was dissolved in DMF (25 mL), and diisopropylethylamine (16.0, 92.7 mmol) and MeI (2.3 mL, 39 mmol) were added. The solid which formed was filtered and the filtrate was concentrated to dryness on a rotary evaporator to provide 15 (1.50 g, 94.3%) as a yellow solid: mp 123°-124° C. (ethanol). The literature (Appleton et al., 1970) reports mp 127° C.

Workup

  1. customThe solid which formed
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-0e3cef2f91ae468d9e3d532552d23f8b
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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