1,2-Naphthoquinone → Benzo[a]phenazine-11-carboxylic acid

HRID 719178

반응식

HRID 719178 반응식
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.C(O)(=O)C.C(O)(=O)C.[NH2:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25].C1C2=C3C(=CC=C2C=CC=1)N=C1C(C=CC=C1C(O)=O)=N3>C(O)(=O)C>[CH:9]1[C:10]2=[C:1]3[C:2](=[CH:3][CH:4]=[C:5]2[CH:6]=[CH:7][CH:8]=1)[N:31]=[C:30]1[C:22]([C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=[CH:29]1)=[N:21]3

참가 물질

5

반응물 3

HCID 106671,2-NaphthoquinoneHCID 13792240Benzo[a]phenazine-8-carboxylic acidHCID 857879142,3-Diamino-benzoic acid, diacetate salt

생성물 1

HCID 13792239Benzo[a]phenazine-11-carboxylic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 1,2-naphthoquinone (commercially available, 2.0 g) and 2,3-diamino-benzoic acid, diacetate salt, (3.79 g) was heated to reflux in acetic acid (30 mL) for 2 hours. The reaction mixture was cooled and the solvent removed in vacuo to yield a gum. This was purified using flash chromatography to yield a 2:1 mixture of the desired title compound to the undesired benzo[a]phenazine-8-carboxylic acid (840 mg). The two isomers were separated after further modification (see Reference Example 3B below).

후처리

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed in vacuo
  4. customto yield a gum
  5. customThis was purified
  6. customto yield

출처 및 근거

ORD 기록
ord-11402d17cad94860b270b072a30f3c74
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132419B2

연결된 노트

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