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

HRID 880495

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-85b8a0bf8f34449ba499ffd3e6cadb34
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993574B2

Linked notes

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