Hydrochloric Acid → 1-Chloro-7-methoxynaphthalene

HRID 895220

反応式

HRID 895220 の反応式
N(OC(C)(C)C)=O.[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2N)=[CH:12][CH:11]=1.[ClH:21]>C(#N)C>[Cl:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[CH:19]=[C:10]([O:9][CH3:8])[CH:11]=[CH:12]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 2358177-Methoxynaphthalen-1-amine

生成物 1

HCID 220481521-Chloro-7-methoxynaphthalene収率 41%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

CuCl2 (4.6 g, 24.6 mmol) and t-butyl nitrite (4.46 g, 43.3 mmol) were added to acetonitrile (125 mL) at 0° C. To this mixture was slowly added a solution of 7-methoxynaphthylamine (4.99 g, 28.8 mmol) in acetonitrile (25 mL). The reaction was allowed to warm to room temperature, stirred with HCl (400 mL of 2N solution) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with 2N HCl, dried over sodium sulfate, filtered, evaporation of the solvent, and purification on a silica column (hexanes) yielded 2.27 g (41%) of an orange liquid. An analytical sample was further purified by reverse phase preparative HPLC to yield the title compound as a yellow solid: mp 32-34° C.;1H NMR (CDCl3): δ 3.98 (3H, s), 7.20 (1H, dd, J=2.52 Hz, J=8.96 Hz), 7.22-7.27 (1H, m), 7.52 (1H, d, J=2.47 Hz), 7.55 (1 h, d, J=7.47 Hz), 7.69 (1H, d, J=8.15 Hz), 7.75 (1H, d, J=8.95 Hz); MS m/z1911193 (M−H)−.

後処理

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic layers were washed with 2N HCl
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporation of the solvent, and purification on a silica column (hexanes)

出典と根拠

ORDレコード
ord-f49cfec9f86e4713b245f5861fa7a3a8
出典データセット
uspto-grants-2005_07
特許番号
US06914074B2

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