Sodium Carbonate → HCID 178513278, compound

HRID 1671562Notes

Reaction equation

HRID 1671562 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([C:21]#[N:22])=[CH:16][CH:15]=[CH:14][C:13]=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+]>C(O)C.O>[OH:25][NH:24][C:21]([C:17]1[C:18]2[CH:19]=[CH:20][C:11]([NH:10][C@H:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)=[N:12][C:13]=2[CH:14]=[CH:15][CH:16]=1)=[NH:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67096021HCID 67096021, compound

Product 1

HCID 178513278HCID 178513278, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of 2-((R)-indan-1-ylamino)-quinoline-5-carbonitrile (example 29, step A) (571 mg, 2.0 mmol), hydroxylamine hydrochloride (514 mg, 7.4 mmol), sodium carbonate (424 mg, 4.0 mmol) in ethanol (7.5 ml) and water (7.5 ml) was heated under reflux conditions for 24 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 (30 ml), dried (MgSO4) and evaporated to yield the crude product as solid which was further purified by crystallization (dichloromethane/methanol) to yield N-hydroxy-2-((R)-indan-1-ylamino)-quinoline-5-carboxamidine as white solid (500 mg, 79%). MS: m/e=319.2 (M+H+); m.p. 200.5° C.

Workup

  1. temperaturewas heated under reflux conditions for 24 h
  2. extractionthe mixture was extracted with ethyl acetate (3×75 ml)
  3. washThe combined organic layers were washed with brine (30 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)

Sources & evidence

ORD record
ord-ad2d58b644844ec9802aeb8791e06d89
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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