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

HRID 270674Notes

Reaction equation

HRID 270674 reaction equation
[CH3:1][O:2][K].[CH:4]1[CH:9]=[C:8](Cl)[CH:7]=[C:6]([C:11]([O:13]O)=O)[CH:5]=1.O=P(Cl)(Cl)Cl.B(Br)(Br)Br.C=O.C(S(N)(=O)=O)C(C)(C)C.CN1C(=O)[N:40]([CH3:43])[CH2:39][CH2:38]C1>C(Cl)Cl.ClCCCl.OS(O)(=O)=O>[O:13]1[C:11]2[C:6]3[CH:5]=[CH:4][CH:9]=[CH:8][C:7]=3[CH:43]=[N:40][C:39]=2[CH2:38][O:2][CH2:1]1

Participants

11

Reactant 7

HCID 712FormaldehydeHCID 24813Phosphorus oxychlorideHCID 25134Boron tribromideHCID 70297m-Chloroperbenzoic acidHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 183484002,2-Dimethylpropane-1-sulfonamideHCID 178502595HCID 178502595, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent2×

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-ee028ef7ed814ea380d35123c1894191
Source dataset
uspto-grants-2008_11
Patent number
US07449479B2

Reaction notes

Loading…