Acetic Acid → 7-Nitro-5-azaphenanthrene-1,10-dicarboxylic Anhydride

HRID 36626

反応式

HRID 36626 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:16](=[N:17][CH:18]=1)[C:15]1=[C:19]3C(C[CH2:10][C:11]3=[CH:12][CH:13]=[CH:14]1)=[CH:7]2)([O-:3])=[O:2].[OH2:20].O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[C:33]([OH:36])(=[O:35])[CH3:34]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:16]([C:15]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:10](=[O:20])[O:36][C:33](=[O:35])[C:34](=[CH:7]2)[C:19]=34)=[N:17][CH:18]=1)([O-:3])=[O:2]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 108005Sodium dichromate dihydrateHCID 233640248-Nitro-10-azaacephenanthrene

生成物 1

HCID 538747207-Nitro-5-azaphenanthrene-1,10-dicarboxylic Anhydride収率 34%

実験手順

8-Nitro-10-azaacephenanthrene (3.0 g, 24 mmol) was heated to 70° C. in acetic acid (100 mL) and sodium dichromate dihydrate (18.0 g, 60.4 mmol) was added. The reaction mixture was heated at reflux for 4 h and poured into ice/water. The precipitated solid was collected and dried in vacuo to obtain 1.64 g (34%) of a yellow solid. The crude material was heated at reflux in a mixture of acetic acid (25 mL) and acetic anhydride (5 mL) for 3 h. The mixture was filtered hot and the collected solid was dried in vacuo to give 0.90 g (17%) of a light brown solid: mp 290°-292° C.; MS m/e 312 (M+NH4+); 1H NMR (DMSO-d6, 300 MHz) δ 8.19 (t, J=4.0 Hz, 1H), 8.73 (d, J=7.3 Hz, 1H), 9.33 (s, 1H), 9.54 (d, J=8.0 Hz, 1H), 9.80 (d, J=2.5 Hz, 1H), 9.90 (d, J=2.0 Hz, 1H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe precipitated solid was collected
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-5cd2018488ff48e08c41bba16cac6f52
出典データセット
uspto-grants-1995_05
特許番号
US05416089

関連ノート

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