Hydrazine hydrate (1:1) → (3-Amino-4-hydroxyphenyl)acetic acid

HRID 651211ノート

反応式

HRID 651211 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O.O.NN>[Pd].[OH-].[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10]

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 4473644-Hydroxy-3-nitrophenylacetic acid

生成物 1

HCID 1473103(3-Amino-4-hydroxyphenyl)acetic acid収率 30%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 14798Sodium Hydroxide溶媒

反応条件

温度
60 °C

実験手順

Compound III was synthesized according to the method of Zupancic and Trpin J. Prac. Chem. 33, 307-308 (1966); CA 66, 37580c. To a stirred solution of sodium hydroxide solution (1 g in 40 ml) in a round bottom flask was added 3-nitro-4-hydroxyphenylacetic acid (4.93 g, 0.025 mol). The solid dissolved at once giving an orange color solution. 10% Pd—C (50 mg) was added followed by dropwise addition of hydrazine monohydrate (3.25 ml). After the completion of the addition (5 minutes), the mixture was heated at 60° C. for 1.5 hr. The temperature was raise to reflux and heating continued for additional 0.5 hr. The solution appeared clear with Pd—C suspended in it. The solution was filtered hot, concentrated to half of the volume and then cooled. The solution was acidified carefully to pH 4-5 with acetic acid. The white precipitate separated after cooling was filtered off and washed with ethanol. m.p. 225-227° C. lit2. 229-230° C. (3.4 g, yield 30%). 1H NMR(D2O, δ) 7.9 (1H, d, j=7 Hz, 6-H); 7.8 (s, 1H, 2-H); 7.65 (1H, d, J=7 Hz, 5-H); 3.4 (2H, s, CH2COOH).

後処理

  1. dissolutionThe solid dissolved
  2. customat once giving an orange color solution
  3. additionAfter the completion of the addition (5 minutes)
  4. temperatureThe temperature was raise
  5. temperatureto reflux
  6. temperatureheating
  7. filtrationThe solution was filtered hot
  8. concentrationconcentrated to half of the volume
  9. temperaturecooled
  10. customThe white precipitate separated
  11. temperatureafter cooling
  12. filtrationwas filtered off
  13. washwashed with ethanol
  14. custom229-230° C. (3.4 g, yield 30%)

出典と根拠

ORDレコード
ord-5b9972267c174a85a52eb88e79bb13a7
出典データセット
uspto-grants-2001_08
特許番号
US06277984B1

反応ノート

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