Sodium Nitrite → HCID 58015549, compound

HRID 422087Notes

Reaction equation

HRID 422087 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]3[O:14][C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)=[CH:16][C:10]=3[C:9]2=[O:24])=[CH:4][C:3]=1[CH3:25].[N:26]([O-])=O.[Na+]>CC(O)=O.O>[Cl:23][C:19]1[CH:18]=[C:17]([C:15]2[O:14][C:11]3[CH:12]=[CH:13][N:8]([C:5]4[CH:4]=[C:3]5[C:2](=[CH:7][CH:6]=4)[NH:1][N:26]=[CH:25]5)[C:9](=[O:24])[C:10]=3[CH:16]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 58015562HCID 58015562, compound

Product 1

HCID 58015549HCID 58015549, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 5-(4-amino-3-methylphenyl)-2-(3-chlorophenyl)furo[3,2-c]pyridine-4(5H)-one (1.02 g, 2.91 mmol) in AcOH (23 mL) was treated with a solution of NaNO2 (0.20 g, 2.9 mmol) in H2O (0.65 mL). After stirring at ambient temperature for 12 h, the reaction mixture was concentrated. The resulting solid was partitioned in CH2Cl2 and water. Any solids were removed by filtration. The filtrate was extracted with CH2Cl2 (4×30 mL). The organics were dried (Na2SO4), filtered, recombined with the removed solids and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MeOH, 100:0 to 90:10) gave the title compound (0.409 g, 40%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 13.29 (s, 1H), 8.17 (m, 1H), 7.96 (t, J=1.8 Hz, 1H), 7.87-7.83 (m, 2H), 7.73-7.71 (m, 2H), 7.65 (d, J=8.7 Hz, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.46-7.43 (m, 1H), 7.38 (dd, J=9.0, 2.1 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe resulting solid was partitioned in CH2Cl2
  3. customAny solids were removed by filtration
  4. extractionThe filtrate was extracted with CH2Cl2 (4×30 mL)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel, CH2Cl2/MeOH, 100:0 to 90:10)

Sources & evidence

ORD record
ord-dd867157474346a7a4ad10b4fcbe12a6
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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