HCID 22285715, compound → HCID 178526399, compound

HRID 1061724Notes

Reaction equation

HRID 1061724 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:14])[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].[N:15]([O-])=O.[Na+]>C(O)(=O)C.O>[N+:1]([C:4]1[CH:13]=[C:12]2[CH2:11][CH2:10][CH2:9][C:8]3=[N:15][NH:14][C:6]([CH:5]=1)=[C:7]23)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 22285715HCID 22285715, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178526399HCID 178526399, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-nitro-5,6,7,8-tetrahydro-naphthalen-1-ylamine (5.9 g, 31.0 mmol) prepared in Step A in glacial acetic acid (100 mL) was added a solution of sodium nitrite (2.13 g, 31.0 mmol) in water (5.0 mL) at 0° C., and the resultant dark solution was stirred at this temperature for 20 h. The volatiles were evaporated and the residue was basified with a saturated solution of sodium bicarbonate (100 mL). The aqueous was extracted with ethyl acetate (4×200 mL) and the combined extracts were washed with brine, dried (MgSO4) and evaporated to a residue that was purified by column chromatography (silica, 20% to 30% gradient of ethyl acetate in hexane) to give an oil (3.8 g, 60%): MS (ES) m/z 204 (M+); 1H NMR (CDCl3) δ 8.22 (1H,s), 7.77 (1H, s), 3.06 (4H, m), 2.26 (2H, m).

Workup

  1. customThe volatiles were evaporated
  2. extractionThe aqueous was extracted with ethyl acetate (4×200 mL)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue that
  6. customwas purified by column chromatography (silica, 20% to 30% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8ea0b5ceacd44c92b40fe09cacff56db
Source dataset
uspto-grants-2005_11
Patent number
US06960608B2

Reaction notes

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