Stannous chloride dihydrate → HCID 59427311, compound

HRID 503576Notes

Reaction equation

HRID 503576 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]2=3)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>CO>[O:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:7]2[CH:19]=[CH:20][C:4]([NH2:1])=[CH:5][CH:6]=2)[C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]1=2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 45881210HCID 45881210, compound

Product 1

HCID 59427311HCID 59427311, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(4-nitrobenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.432 g, 1.6 mmol) and tin(II) chloride dihydrate (1.8 g, 8.0 mmol) in MeOH (10 mL) was heated to 50° C. After 3 hrs the mixture was concentrated in vacuo and the residue taken up in EtOAc. Saturated NaHCO3 was added and the mixture was filtered. The filtrate was washed with brine, dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography using 20-100% Hexanes:EtOAc to afford 4-((2,3-dihydrobenzo[b][1,4]oxazin-4-yl)methyl)benzenamine as an orange oil. MS found: M+H+=241.1.

Workup

  1. concentrationAfter 3 hrs the mixture was concentrated in vacuo
  2. additionSaturated NaHCO3 was added
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f0274978029142dca0ea0339b2f501c4
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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