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3-Nitrobenzoic acid → Biphenyl indolizinyl nitrobenzoate

HRID 22055
Notes
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Reaction equation

HRID 22055 reaction equation
N([C:8]([O:10]CC)=[O:9])=NC(OCC)=O.[N+:13](C1C=C(C=CC=1)C(O)=O)([O-:15])=[O:14].O[C:26]1N=N[NH:29][CH:30]=1.[C:31]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC.C(OCC)(=O)C>[C:31]1([C:37]2[C:38]([N+:13]([O-:15])=[O:14])=[C:39]([CH:40]=[CH:41][CH:42]=2)[C:8]([OH:10])=[O:9])[CH:26]=[CH:30][N:29]2[C:36]=1[CH:35]=[CH:34][CH:33]=[CH:32]2.[C:31]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 84973-Nitrobenzoic acidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516797HCID 178516797, compound

Product 1

HCID 86748744Biphenyl indolizinyl nitrobenzoate

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent2×
HCID 8857Ethyl AcetateSolvent

Procedure

Alternatively, the biphenyl trans-hydroxy triazole can be prepared using the Mitsunobu reaction conditions. To a solution of diethyl azodicarboxylate (2.0 mmol) and 3-nitrobenzoic acid (2.0 mmol) in 2.0 mL of THF is added dropwise a solution of the biphenyl hydroxy triazole (2.0 mmol, obtained from Step 1 of Example 3224), and triphenylphosphine (2.0 mmol) in 1.0 mL of THF at room temperature. The resulting solution is stirred at room temperature until the reaction is complete. The resulting mixture is diluted with ether or ethyl acetate, and washed with water. The extracts are dried (MgSO4) and concentrated in vacuo to give the biphenyl indolizinyl nitrobenzoate. The crude benzoate is hydrolyzed with LiOH in aqueous THF at room temperature and purified to give the biphenyl trans-hydroxy triazole.

Workup

  1. customthe Mitsunobu reaction conditions
  2. washwashed with water
  3. dry with materialThe extracts are dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23ceeef732bc4310a67a7ccc06fd3328
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05426105

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes