Sodium Carbonate → HCID 178513220, compound

HRID 1695680Notes

Reaction equation

HRID 1695680 reaction equation
[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:15]=3[N:16]=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:19]1[CH:18]=[CH:17][C:15]2[N:16]=[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)[O:12][CH2:13][C:14]=2[CH:20]=1)=[NH:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 178509458HCID 178509458, compound

Product 1

HCID 178513220HCID 178513220, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of 2-((R)-indan-1-ylamino)-4H-benzo[d][1,3]oxazine-6-carbonitrile (example 117) (310 mg, 1.07 mmol), hydroxylamine hydrochloride (275 mg, 3.96 mmol), sodium carbonate (227 mg, 2.14 mmol) in ethanol (4 ml) and water (4 ml) was heated under reflux conditions for 17 h, water (10 ml) was added, the precipitate was collected by filtration, washed with water and hexane. The crude product was further purified by crystallization (diethyl ether/methanol 10:1) to yield the title compound as white solid (280 mg, 81%). MS (ISP): m/e=323.3 (M+H+); m.p. 206° C.

Workup

  1. temperaturewas heated under reflux conditions for 17 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water and hexane
  4. customThe crude product was further purified by crystallization (diethyl ether/methanol 10:1)

Sources & evidence

ORD record
ord-0d7c6e87e6ea4724ab56dce391d79c88
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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