Hydrochloric Acid → HCID 68527980, compound

HRID 2246901Notes

Reaction equation

HRID 2246901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[CH:13][N:14](C)[C:10]=2[C:9]=1[C:18]#[N:19].Cl.[N:21]([O-])=O.[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[N:21][N:14]([CH3:13])[C:10]=2[C:9]=1[C:18]#[N:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11543555HCID 11543555, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 68527980HCID 68527980, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate of Example 8B (126 mg, 0.49 mmol) was stirred in THF (3 mL) with water (2 mL) and 1N HCl (1 mL) at 0° C. Sodium nitrite (37 mg, 0.54 mmol) in water (0.5 mL) was added dropwise, and the reaction stirred for 30 min. The solution was quenched with sat. NaHCO3 solution and extracted with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (40% EtOAc/hexanes) gave 102 mg (78%) of the title compound as a pale orange solid. 1H NMR (400 MHz, CDCl3): δ 8.31 (d, 1H, J=8.4 Hz), 7.39-7.58 (m, 5H), 4.61 (s, 3H). MS (ES) [m+H] calc'd for C14H9N4Cl, 269, 271; found 269, 271.

Workup

  1. customThe solution was quenched with sat. NaHCO3 solution
  2. extractionextracted with EtOAc
  3. dry with materialOrganics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a88d1adb9eee44ca96826171bc56e307
Source dataset
uspto-grants-2010_03
Patent number
US07687638B2

Reaction notes

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