Anthranilic Acid → 2-Azidobenzoic acid

HRID 856909ノート

反応式

HRID 856909 の反応式
N([O-])=O.[Na+].[C:5]([OH:14])(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[NH2:8].[N-:15]=[N+:16]=[N-].[Na+].O.O.O.C([O-])(=O)C.[Na+]>O.Cl>[N:8]([C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[C:5]([OH:14])=[O:13])=[N+:15]=[N-:16]

参加物

7

反応物 4

HCID 227Anthranilic AcidHCID 33557Sodium AzideHCID 23665404Sodium Acetate TrihydrateHCID 23668193Sodium Nitrite

生成物 1

HCID 53255602-Azidobenzoic acid収率 490.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒3 回

実験手順

A solution of sodium nitrite (4.75 g, 0.07 mol) in water (63 mL) was added dropwise to a stirred solution of anthranilic acid (10 g, 0.07 mol) in concentrated HCl (125 mL) and water (125 mL), maintaining the temperature below 5° C. After addition the mixture was stirred for 10 min then rapidly filtered. The solution was transferred to a dropping funnel and added dropwise to a solution of NaN3 (4.2 g, 0.065 mol) and sodium acetate trihydrate (105 g, 0.77 mol) in water (125 mL). After addition the mixture was stirred at 0° C. for 15 min then at room temperature for 35 min. The suspension was filtered and washed with water. The solid was then dissolved in EtOAc, dried (MgSO4) and the solvent evaporated. The title compound (52 g, 49%) was isolated as a cream solid. 1H NMR (360 MHz, CDCl3) δ 7.24–7.29 (2H, m), 7.62 (1H, d of t, J=8.1 and 1.5 Hz), 8.12 (1H, d of d, J=7.7, and 1.6 Hz).

後処理

  1. temperaturemaintaining the temperature below 5° C
  2. additionAfter addition the mixture
  3. filtrationthen rapidly filtered
  4. customThe solution was transferred to a dropping funnel
  5. additionAfter addition the mixture
  6. stirringwas stirred at 0° C. for 15 min
  7. waitat room temperature for 35 min
  8. filtrationThe suspension was filtered
  9. washwashed with water
  10. dissolutionThe solid was then dissolved in EtOAc
  11. dry with materialdried (MgSO4)
  12. customthe solvent evaporated

出典と根拠

ORDレコード
ord-5c88ff188b5148d096250c6960abd128
出典データセット
uspto-grants-2006_12
特許番号
US07144887B2

反応ノート

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