Acetic Acid → 2,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile

HRID 1072256

反応式

HRID 1072256 の反応式
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=O)[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14]([CH2:20][C:21]#[N:22])=[C:15]([C:18]#[N:19])[C:16]#[N:17].C(O)(=O)C.C([SiH](CC)CC)C>C(O)C>[NH2:17][C:16]1[N:22]=[C:21]2[O:12][C:7]3[C:8]([CH2:9][C:20]2=[C:14]([NH2:13])[C:15]=1[C:18]#[N:19])=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3

参加物

6

反応物 4

HCID 176Acetic AcidHCID 12052TriethylsilaneHCID 133562-Amino-1-propene-1,1,3-tricarbonitrileHCID 668085-Nitrosalicylaldehyde

生成物 1

HCID 100852162,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile収率 60.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
66 °C

実験手順

5-nitrosalicylaldehyde (132 mmol, 22.00 g), 2-amino-1-propene-1,1,3-tricarbonitrile (132 mmol, 17.39 g), acetic acid (31 mL), and ethanol (500 mL) were combined and heated to reflux overnight. The resulting slurry was concentrated in vacuo and then dissolved in trifluoroacetic acid (350 mL) at 0° C. Triethylsilane (1.40 mol, 162 g, 225 mL) was added. The mixture was heated overnight at 66° C. The mixture was cooled and concentrated in vacuo. Triturating with methanol gave 2,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile as a yellow solid (22.48 g, 60% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.13 (d, J=9.0 Hz, 1H), 8.00 (s, 1H), 7.25 (d, J=9.0 Hz, 1H), 6.70 (br s, 2H), 6.50 (bs, 2H), 3.82 (s, 2H); m/z 284 (M+H); Anal. Calcd for C13H9N5O3-0.5H2O: C, 53.43; H, 3.45; N, 23.96, found: C, 53.41; H, 3.17; N, 23.71.

後処理

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe resulting slurry was concentrated in vacuo
  4. dissolutiondissolved in trifluoroacetic acid (350 mL) at 0° C
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated in vacuo
  7. customTriturating with methanol

出典と根拠

ORDレコード
ord-21aa34e5307d4a42b6ff494b6da06da1
出典データセット
uspto-grants-2005_06
特許番号
US06909001B2

関連ノート

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