Formaldehyde → 4H-[1,3]dioxino[5,4-c]isoquinolin

HRID 1893003Notes

Reaction equation

HRID 1893003 reaction equation
CO[K].[CH:4]1[CH:9]=[C:8](Cl)[CH:7]=[C:6]([C:11](OO)=O)[CH:5]=1.O=P(Cl)(Cl)Cl.B(Br)(Br)Br.[CH2:24]=[O:25].C(S([NH2:34])(=O)=O)C(C)(C)C.[CH:35]1([C:38](S(N)(=O)=O)=[O:39])C[CH2:36]1>CN1C(=O)N(C)CCC1.C(Cl)Cl.ClCCCl.OS(O)(=O)=O>[O:25]1[C:36]2[C:5]3[CH:4]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:11]=[N:34][C:35]=2[CH2:38][O:39][CH2:24]1

Participants

12

Reactant 7

HCID 712FormaldehydeHCID 24813Phosphorus oxychlorideHCID 25134Boron tribromideHCID 70297m-Chloroperbenzoic acidHCID 183484002,2-Dimethylpropane-1-sulfonamideHCID 57254296Cyclopropylcarbonyl-sulfonamideHCID 178502595HCID 178502595, compound

Product 1

HCID 703294834H-[1,3]dioxino[5,4-c]isoquinolin

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Reaction Conditions: (1) MeOK in DMPU; (2) MCPBA in CH2Cl2; (3) POCl3 in DCE; (4) BBr3 in CH2Cl2; (5) HCHO solution in 40% H2SO4 by procedure of Synthesis of 1,3-oxazino[5,6-c]isoquinolines and related compounds. Miyoko Toyama and Hirotaka Otomasu, Chem. Pharm. Bull. 33(12), 5543-5546, 1985; (6) Fluororination procedure by Uchibori, Y.; Umeno, M.; Yoshiokai, H.; Heterocycles, 1992, 34 (8), 1507-1510

Workup

  1. customReaction Conditions

Sources & evidence

ORD record
ord-7ffbb7627bd142e2b732c98de266c471
Source dataset
uspto-grants-2013_08
Patent number
US08507722B2

Reaction notes

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