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

HRID 880495

반응식

HRID 880495 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85b8a0bf8f34449ba499ffd3e6cadb34
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

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