Anthranilic Acid → HCID 23540710、化合物

HRID 416636

反応式

HRID 416636 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[OH:8].[NH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=O>>[O:8]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[N:1]=[C:12]1[C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[NH2:9]

参加物

3

反応物 2

HCID 227Anthranilic AcidHCID 2333923-Amino-4-hydroxypyridine

生成物 1

HCID 23540710HCID 23540710、化合物収率 39.3%

実験手順

3-Amino-4-hydroxypyridine (2.225 g, 20.0 mmol) and 2-aminobenzoic acid (2.740 g, 20.0 mmol) were stirred in polyphosphoric acid (40 mL) at 140° C. for 6 hrs. The reaction mixture was poured into distilled water and sodium hydroxide was added until pH=8. The precipitate was collected by filtration and the crude product was purified by chromatography on silica gel eluting with petroleum ether:ethyl acetate:Et3N (160:40:1) to give 2-(oxazolo[4,5-c]pyridin-2-yl)benzenamine (1.659 g, Yield: 39%). 1H NMR (400 MHz, DMSO-d6) δ: 6.68 (1H, t, J=7.6 Hz), 6.93 (1H, d, J=8.0 Hz), 7.17 (2H, s), 7.30 (1H, t, J=7.6 Hz), 7.83 (1H, d, J=5.6 Hz), 7.90 (1H, d, J=8.0 Hz), 8.55 (1H, d, J=5.6 Hz), 9.05 (1H, s); MS (ESI) calcd. for C12H9N3O (m/z): 211. found: 212 [M+1]+.

後処理

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water and sodium hydroxide
  3. additionwas added until pH=8
  4. filtrationThe precipitate was collected by filtration
  5. customthe crude product was purified by chromatography on silica gel eluting with petroleum ether:ethyl acetate:Et3N (160:40:1)

出典と根拠

ORDレコード
ord-89d9006bfad24159940d030983ed4e04
出典データセット
uspto-grants-2012_01
特許番号
US08088928B2

関連ノート

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