Ammonium Hydroxide → HCID 17966018, compound

HRID 2253329Notes

Reaction equation

HRID 2253329 reaction equation
Cl[CH:2]([C:11]1[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[NH4+:17].[OH-]>C1COCC1.ClCCl>[NH2:17][CH:2]([C:11]1[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 17965929HCID 17965929, compound

Product 1

HCID 17966018HCID 17966018, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example 41E (200 mg, 0.746 mmol) in THF (5 mL) at room temperature was treated dropwise with concentrated NH4OH (2.0 mL), stirred for 2 hours, diluted with dichloromethane, washed with water, dried (MgSO4), filtered, and concentrated to provide 123 mg (77%) of the desired product. MS (ESI) m/z 213 (M+H)+; 1H NMR (CDCl3) δ 7.65 (m, 2H), 7.48 (m, 2H), 7.39 (s, 1H), 6.84 (s, 1H), 5.26 (s, 1H), 3.49 (s, 3H).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18b3ae0d1397483783fdc54f4a714697
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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