Oxalyl chloride → 5-tert-Butyl-N-cyclopropyl-2-methoxy-3-nitro-benzamide

HRID 598728Notes

Reaction equation

HRID 598728 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CC[N:27]([CH:31]([CH3:33])[CH3:32])C(C)C.C1(N)CC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([NH:27][CH:31]1[CH2:33][CH2:32]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 508823195-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid

Product 1

HCID 574185525-tert-Butyl-N-cyclopropyl-2-methoxy-3-nitro-benzamideYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-t-butyl-2-methoxy-3-nitrobenzoic acid (759 mg, 3 mmol) in 18 mL DCM, oxalyl chloride (1.8 mL, 15 mmol) was added. After stirring at rt for 2 hr the reaction mixture was concentrated to dryness. The resulting acid chloride was dissolved in 30 mL DCM, and DIEA (2.6 mL, 15 mmol) and cyclopropyl amine (0.83 mL, 12 mmol) were added. Stirring was continued overnight at rt, after which DCM was added to the reaction mixture. After aq. sodium bicarbonate work-up, column chromatography purification was performed on ISCO Optix (3×12 g silica gel column) using DCM. 678 mg pure product was isolated as pale yellow solid. Calculated mass=292. Observed mass=295

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe resulting acid chloride was dissolved in 30 mL DCM
  3. stirringStirring
  4. waitwas continued overnight at rt
  5. customcolumn chromatography purification

Sources & evidence

ORD record
ord-02d0af33656b4469832d4d34ce08199b
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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