Sodium Carbonate → HCID 178513233, compound

HRID 1931506Notes

Reaction equation

HRID 1931506 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[N:22])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[OH:25][NH:24][C:21]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:10][C@H:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]1)[CH:20]=[CH:19]2)=[NH:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 68630708HCID 68630708, compound

Product 1

HCID 178513233HCID 178513233, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of 2-((R)-indan-1-ylamino)-quinoline-6-carbonitrile (143 mg, 0.5 mmol), hydroxylamine hydrochloride (129 mg, 1.86 mmol), sodium carbonate (106 mg, 1.0 mmol) in EtOH (2 ml) and water (2 ml) was heated under reflux conditions for 6 h, water (40 ml) was added, and the mixture was extracted with ethyl acetate (3×75 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated to yield the crude product as solid which was further purified by crystallization (dichloromethane/methanol/heptane) to yield N-hydroxy-2-((R)-indan-1-ylamino)-quinoline-6-carboxamidine as off-white solid (140 mg, 88%).

Workup

  1. temperaturewas heated under reflux conditions for 6 h
  2. extractionthe mixture was extracted with ethyl acetate (3×75 ml)
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto yield the crude product as solid which
  7. customwas further purified by crystallization (dichloromethane/methanol/heptane)

Sources & evidence

ORD record
ord-2d3d854887a64170ba3d45f860cfc79b
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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