Water → HCID 13222960, compound

HRID 1111871Notes

Reaction equation

HRID 1111871 reaction equation
[O:1]1[CH:3]2[C:4]3[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:5]=3[O:6][C:7]([CH3:9])([CH3:8])[CH:2]12.Cl.[Cl:18][CH2:19][CH2:20][CH2:21][NH2:22].[OH-].[Na+].O>O1CCOCC1.C(OCC)(=O)C>[ClH:18].[Cl:18][CH2:19][CH2:20][CH2:21][NH:22][C@H:3]1[C@H:2]([OH:1])[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:4]1=2

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 114690951-Propanamine, 3-chloro-, hydrochlorideHCID 13222921HCID 13222921, compound

Product 1

HCID 13222960HCID 13222960, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3,4-Epoxy-3,4-dihydro-2,2-dimethyl-6-nitro-2H-benzo[b]pyran (0.50g.), prepared as described in British Pat. No. 1,495,526, chloropropylamine hydrochloride (0.65g.), and sodium hydroxide pellets (0.20g.) in dioxan (25 ml) and water (3 ml) were stirred at room temperature for 6 days. Dilution with water and isolation via ethyl acetate gave a gum (0.62g.) which was separated, by application to silica gel plates and development with ethyl acetate- 60-80° petroleum ether mixture, into starting epoxide (0.34g.) and an amine fraction (0.25g.). The latter was dissolved in diethyl ether and treated with ethereal hydrogen chloride to give trans-4-(3-chloropropylamino)-3,4-dihydro-2,2-dimethyl-6-nitro-2H-benzo[b]-pyran-3-ol hydrochloride (0.15g.); m.p. 242°-243°.

Workup

  1. customwas separated, by application to silica gel plates and development with ethyl acetate- 60-80° petroleum ether mixture
  2. dissolutionThe latter was dissolved in diethyl ether
  3. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-efbe12e668f6436da3691a6391e8ea07
Source dataset
uspto-grants-1978_10
Patent number
US04119643

Reaction notes

Loading…