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

HRID 567730
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HRID 567730 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-78 °C

실험 절차

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, 25 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.

후처리

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

출처 및 근거

ORD 기록
ord-75e30992a0904fd99d164efa7aaa9b70
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06180632B2

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