Formic Acid → HCID 58636760, compound

HRID 1158960Notes

Reaction equation

HRID 1158960 reaction equation
C[O:2][C:3](=O)[N:4]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[C:5]1[CH:10]=[N:9][C:8]([CH3:11])=[C:7]2[O:12]C(C)(C)[O:14][CH2:15][C:6]=12.C(O)=O>C(O)C>[OH:12][C:7]1[C:6]2[CH2:15][O:14][C:3](=[O:2])[N:4]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[C:5]=2[CH:10]=[N:9][C:8]=1[CH3:11]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 58636829HCID 58636829, compound

Product 1

HCID 58636760HCID 58636760, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The hydrolysis of (4-cyano-benzyl)-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-carbamic acid methyl ester (81) (5.1 g, 13.9 mmol) and subsequent cyclization was achieved by heating 81 in a 1:1 mixture of aqueous formic acid (20%) and ethyl alcohol at 80° C. for 2 hours. The evaporation of solvent, followed by the addition of water precipitated the product 4-(5-hydroxy-6-methyl-2-oxo-4H-pyrido[3,4-d][1,3]oxazin-1-ylmethyl)-benzonitrile (82) (2.8 g, 74% yield).

Workup

  1. temperatureby heating 81
  2. customThe evaporation of solvent
  3. additionfollowed by the addition of water

Sources & evidence

ORD record
ord-1242ee6a08a04d41bdcec9cfaa76c95f
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

Loading…