HCID 22147962, compound → HCID 22147940, compound

HRID 1823921Notes

Reaction equation

HRID 1823921 reaction equation
[CH3:1][C:2]1[C:3]([NH2:17])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[N:18]([O-])=O.[Na+]>C(O)(=O)C>[N+:8]([C:6]1[CH:7]=[C:2]2[C:3](=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=1)[NH:17][N:18]=[CH:1]2)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 22147962HCID 22147962, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22147940HCID 22147940, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-Methyl-5-nitro-biphenyl-2-ylamine (91 mg, 0.39 mmole) in pre-heated glacial acetic acid (4 mL) was added 0.44M sodium nitrite solution (1 mL), in a dropwise fashion. The resulting mixture was stirred overnight at room temperature. The crude product was concentrated in-vacuo and the residue re-dissolved in EtOAc (20 mL) and washed with saturated NaHCO3 (2×20 mL) and brine (1×20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in-vacuo to yield the desired product (67 mg) as a yellow powder. 1H NMR (400 MHz, CDCl3) δ 7.50(1H, m), 7.58(2H, m), 7.69(2H, m), 8.33 (2H, m), 8.75(1H, s), 10.55(br s). MS (ES+): m/e=240, (ES−): m/e=238.

Workup

  1. concentrationThe crude product was concentrated in-vacuo
  2. dissolutionthe residue re-dissolved in EtOAc (20 mL)
  3. washwashed with saturated NaHCO3 (2×20 mL) and brine (1×20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-4c3affe755bb415d8b3fded218453ced
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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