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4-Nitrobenzoic Acid → Cyclohex-3-enyl-(6,7-dimethoxyquinoxalin-2-yl)-amine

HRID 2415655
Notes
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Reaction equation

HRID 2415655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19](O)[CH2:18][CH2:17]1)[CH:7]=[N:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>C1COCC1>[CH:16]1([NH:15][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)[CH2:21][CH2:20][CH:19]=[CH:18][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178486821HCID 178486821, compound

Product 1

HCID 22573157Cyclohex-3-enyl-(6,7-dimethoxyquinoxalin-2-yl)-amineYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

To a solution of trans-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanol (303 mg, 1 mmol) in 10 mL of THF at −78° C. are added triphenylphosphine (524 mg, 2 mmol) and diethyl azodicarboxylate (1 mL). The mixture is stirred at −78° C. for one hour before addition of 4-nitrobenzoic acid (334 mg, 2 mmol). After being stirred at −78° C. for one hour, the mixture is continued to stir at ROOM TEMPERATURE for additional hour and then concentrated. The residue is chromatographed on silica gel (ether) to give 250 mg (87.7%) of cyclohex-3-enyl-(6,7-dimethoxyquinoxalin-2-yl)-amine.

Workup

  1. stirringto stir at ROOM TEMPERATURE for additional hour
  2. concentrationconcentrated
  3. customThe residue is chromatographed on silica gel (ether)

Sources & evidence

ORD record
ord-a2dd51bce6354a219ee60770aee31689
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06821962B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes