1,5-Dinitronaphthalene → 1-Naphthalenamine, 5-nitro-

HRID 880495

反応式

HRID 880495 の反応式
[S-2].[Na+].[Na+].C(=O)(O)[O-].[Na+].[N+:9]([C:12]1[C:21]2[C:16](=[C:17]([N+:22]([O-])=O)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)([O-:11])=[O:10]>O.CO>[N+:9]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH:20]=[CH:19][CH:18]=[C:17]2[NH2:22])([O-:11])=[O:10]

参加物

6

反応物 3

HCID 118031,5-DinitronaphthaleneHCID 14804Sodium SulfideHCID 516892Sodium Bicarbonate

生成物 1

HCID 767591-Naphthalenamine, 5-nitro-収率 42%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A 70° C. solution of sodium sulfide (3.17 g, 32.97 mmol) and sodium bicarbonate in water (7 mL) was added dropwise to suspension of 1,5-dinitro naphthalene (2.0 g, 9.16 mmol) in methanol (30 mL) at reflux and the resultant mixture was stirred for 5 min. The mixture was cooled to 0° C., quenched with ice and stirred for a further 10 min followed by acidification with concentrated hydrochloric acid. The resulting mixture was stirred for 30 min then washed with ethyl acetate (2×50 mL). The aqueous layer was basified with aqueous ammonia and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (2×50 mL), brine (2×50 mL), dried over anhydrous sodium sulphate, filtrated and concentration in vacuo afforded of 5-nitronaphthalen-1-amine (710 mg, 42%) as a brown solid.

後処理

  1. temperatureat reflux
  2. customquenched with ice
  3. stirringThe resulting mixture was stirred for 30 min
  4. washthen washed with ethyl acetate (2×50 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe combined organic layers were washed with water (2×50 mL), brine (2×50 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltrated
  9. concentrationconcentration in vacuo

出典と根拠

ORDレコード
ord-85b8a0bf8f34449ba499ffd3e6cadb34
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

関連ノート

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