N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide → 3-fluoro-N-(2-hydroxyphenyl)isonicotinamide

HRID 1946634ノート

反応式

HRID 1946634 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[F:23])C1C=CC=CC=1>Br.C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>[F:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8])=[O:24]

参加物

6

反応物 1

HCID 59783597N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide

生成物 1

HCID 597834993-fluoro-N-(2-hydroxyphenyl)isonicotinamide収率 84.3%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 260Hydrogen Bromide溶媒HCID 962Water溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

Title compound 445 (1.99 g, 6.18 mmol) was dissolved in the solution of HBr (33% in AcOH, 15.0 mL) and acetic acid (10.0 mL). The reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with water and basified with solid sodium bicarbonate until alkaline. More water was added to dissolve the salt and the aqueous layer was extracted with ethyl acetate (twice). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was triturated in 30% ethyl acetate in hexanes to afford title compound 446 (1.21 g, 84%) as a beige-yellow solid. 1H NMR (DMSO-d6) δ (ppm): 10.02 (s, 1H), 9.75 (s, 1H), 8.75 (d, J=2.0 Hz, 1H), 8.59 (dd, J=4.8, 1.3 Hz, 1H), 7.94 (dd, J=8.0, 1.6 Hz, 1H), 7.76 (dd, J=6.1, 4.9 Hz, 1H), 7.03 (ddd, J=8.0, 7.4, 1.6 Hz, 1H), 6.92 (dd, J=8.0, 1.4 Hz, 1H), 6.84 (td, J=7.6, 1.3 Hz, 1H). MS (m/z): 233.2 (M+H).

後処理

  1. dissolutionto dissolve the salt
  2. extractionthe aqueous layer was extracted with ethyl acetate (twice)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated in 30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-02f3108d5b3b490c8e63d0b7360a8c8b
出典データセット
uspto-grants-2013_03
特許番号
US08399452B2

反応ノート

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