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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Hydroxy-4-nitro-benzoic acid tert-butyl ester

HRID 714851
Notes
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Reaction equation

HRID 714851 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N=C=N[CH2:19][CH2:20][CH2:21]N(C)C)C.ON1C2C=CC=C[C:29]=2N=N1.C(=O)([O-])O.[Na+]>C(O)(C)(C)C.C(N(CC)CC)C>[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:20]([CH3:21])([CH3:29])[CH3:19])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692664-Nitrosalicylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 716010782-Hydroxy-4-nitro-benzoic acid tert-butyl esterYield 35.2%

Reagents, catalysts & solvents 2

HCID 6386
tert-Butanol
Solvent
HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-hydroxy-4-nitrobenzoic acid (5.0 g) in tert-butyl alcohol (100 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.4 g), 1-hydroxybenzotriazole (3.7 g) and triethylamine (7.6 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.3 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0dcf3759e4894e51a8bd95d0a14d02f9
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187453B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes