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

HRID 719178

反応式

HRID 719178 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11402d17cad94860b270b072a30f3c74
出典データセット
uspto-grants-2006_11
特許番号
US07132419B2

関連ノート

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