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

HRID 1072256

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HRID 1072256 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
66 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-21aa34e5307d4a42b6ff494b6da06da1
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06909001B2

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