Formaldehyde → HCID 15881114, compound

HRID 1614203Notes

Reaction equation

HRID 1614203 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.N1CCC[C@H:22]1C(O)=O.C=O>C(#N)C>[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH:16]([CH2:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][CH:6]=2)[C:14](=[O:15])[O:13]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 249055-BromoindoleHCID 145742L-Proline

Product 1

HCID 15881114HCID 15881114, compoundYield 417.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-bromoindole (10.07 g, 51 mmol), Meldrum's acid (7.38 g, 51 mmol), proline (1.24 g), and 5.2 ml of 30% aqueous formaldehyde in 100 ml of acetonitrile was allowed to stand at room temperature for 24 hours. The acetonitrile was removed in vacuo. Crystallization of the product from methanol (50 ml) provided 15.83 g of 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)methyl-5-bromoindole as a white solid.

Workup

  1. customThe acetonitrile was removed in vacuo
  2. customCrystallization of the product from methanol (50 ml)

Sources & evidence

ORD record
ord-c014d8ab7045482ab5200cc8f45f0a0f
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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