Water → t-Butyl 4-(methylamino)methyl-3-nitrobenzoate

HRID 2186053Notes

Reaction equation

HRID 2186053 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17].O.[CH3:20][N:21](C=O)C>>[CH3:20][NH:21][CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 18462578t-Butyl 4-bromomethyl-3-nitrobenzoate

Product 1

HCID 22451930t-Butyl 4-(methylamino)methyl-3-nitrobenzoateYield 36%

Procedure

Anhydrous methylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min. A solution of t-butyl 4-bromomethyl-3-nitrobenzoate (5.0 g, 15.8 mmol) (Int. J. Peptide. Res., 36, 31 (1990)) in DMF (10 mL) was added dropwise to the cold amine solution. The solution was stirred at 0° for 30 min and poured into water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water, dried (sodium sulfate) and concentrated to give a yellow-brown oil. The oil was purified by chromatography (silica gel, 3% isopropanol/CH2Cl2) to give the title compound (1.5 g, 36%). 1H NMR (400 MHz, CDCl3) δ8.5 (s, 1H), 8.2 (d, 1H), 7.7 (d, 1H), 4.05 (s, 2H), 2.5 (s, 3H), 1.6 (s, 9H).

Workup

  1. customAnhydrous methylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a yellow-brown oil
  7. customThe oil was purified by chromatography (silica gel, 3% isopropanol/CH2Cl2)

Sources & evidence

ORD record
ord-f68527a580b748d8b80d2723b742086d
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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