Triethylamine → Methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate

HRID 852581Notes

Reaction equation

HRID 852581 reaction equation
[NH2:1][C:2]1[C:3]([F:15])=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CCN(CC)CC.[Cl:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:23][CH2:24][CH2:25][CH2:26][C:27]([NH:1][C:2]1[C:3]([F:15])=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 63022631Methyl 3-amino-2-fluoro-5-nitrobenzoate

Product 1

HCID 69358882Methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-amino-2-fluoro-5-nitrobenzoate (D138) (12 g, 56 mmol, 1 equiv) in CH2Cl2 (150 ml) at room temperature were added NEt3 (11.7 ml, 84 mmol, 1.5 equiv) and 4-chlorobutanoyl chloride (6.9 ml, 61.6 mmol, 1.1 equiv) and the resulting mixture was stirred for 2 h then washed with a 2N aqueous HCl solution and a saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4/1) gave methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate (D139) (16.2 g, 91%) as a yellow solid. [M+H]+=319.1, RT=3.12 min.

Workup

  1. washthen washed with a 2N aqueous HCl solution
  2. dry with materiala saturated aqueous NaHCO3 solution, dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4/1)

Sources & evidence

ORD record
ord-da73498e048249afa346cb165be74f26
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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