Water → HCID 59645475, compound

HRID 2253309Notes

Reaction equation

HRID 2253309 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.CCN(CC)CC.O>C1COCC1>[Cl:15][C:8]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 13382400Methyl 2,6-dichloro-3-nitrobenzoate

Product 1

HCID 59645475HCID 59645475, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2,6-dichloro-3-nitrobenzoate (11.9 g, 47.4 mmol), p-methoxybenzylamine (8.13 g, 59.3 mmol; additional amounts of 1.63 g, 11.9 mmol added after 5 and 6.5 h), and Et3N (7.20 g, 71.1 mmol; additional amount of 1.20 g, 11.9 mmol added after 6.5 h) in THF (190 mL) was stirred at room temperature for 15 min then was heated to reflux for 10 h. Water (100 mL) was added to the mixture and most of the THF was removed under reduced pressure. The residue was partitioned between aqueous 1 N HCl solution (350 mL) and EtOAc (500 mL). The organic layer was washed with aqueous 1 N HCl solution (100 mL) and brine (100 mL), then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 6:1) to give the title compound (13.2 g, 79% yield) as a yellow solid.

Workup

  1. temperaturethen was heated
  2. temperatureto reflux for 10 h
  3. customwas removed under reduced pressure
  4. customThe residue was partitioned between aqueous 1 N HCl solution (350 mL) and EtOAc (500 mL)
  5. washThe organic layer was washed with aqueous 1 N HCl solution (100 mL) and brine (100 mL)
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 6:1)

Sources & evidence

ORD record
ord-b22b2b8be71345268078b29af07d69dc
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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