Acetic Acid → Pyrazino[2,3-alpha]phenazine-11-carboxylic acid

HRID 1267001ノート

反応式

HRID 1267001 の反応式
[N+](C1C(N[C:14]2[CH:23]=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=C(C=CC=1)C(O)=O)([O-])=O.[BH4-].[Na+].[CH3:26][C:27]([OH:29])=[O:28]>[OH-].[Na+].O>[N:15]1[C:20]2=[C:21]3[C:16](=[CH:17][CH:18]=[C:19]2[N:22]=[CH:23][CH:14]=1)[N:15]=[C:14]1[C:23]([C:26]([C:27]([OH:29])=[O:28])=[CH:17][CH:16]=[CH:21]1)=[N:22]3

参加物

6

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 185454443-Nitro-(quinoxalinylamino)benzoic acid

生成物 1

HCID 11065679Pyrazino[2,3-alpha]phenazine-11-carboxylic acid収率 73%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 3-nitro-(quinoxalinylamino)benzoic acid (0.8 g, 2.58 mmol) in 5M NaOH (40 mL) was treated with NaBH4 (0.9 g, 12.9 mmol), and the mixture was heated under reflux for 2 h. The cooled mixture was diluted with water (40 mL), then neutralized with glacial AcOH to give pyrazino[2,3-α]phenazine-11-carboxylic acid (0.52 g, 73%): mp (MeOH/Et3N/AcOH)>350° C. 1H NMR [CF3CO2D] δ 8.62 (dd, J=8.8, 7.3 Hz, 1 H, H-9), 8.91 (d, J=9.8 Hz, 1 H, H-5 or H-6), 8.97 (d, J=9.8 Hz, H-5 or H-6), 9.18 (dd, J=8.8, 1.0 Hz, 1 H, H-8), 9.47 (dd, J=7.3, 1.0 Hz, 1 H, H-10), 9.57 (d, J=2.2 Hz, 1 H, H-2 or H-3), 9.65 (d, J=2.2 Hz, 1 H, H-2 or H-3),

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h

出典と根拠

ORDレコード
ord-1d64343d3ed34cc7a915c3ab6851970e
出典データセット
uspto-grants-2003_04
特許番号
US06552021B2

反応ノート

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