Formaldehyde → HCID 23149206, compound

HRID 1983048Notes

Reaction equation

HRID 1983048 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].[CH2:12]=[O:13].C(N(CC)CC)C>CC(C)=O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][OH:13])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 2302823-Cyanoindole

Product 1

HCID 23149206HCID 23149206, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 1.42 g of 3-cyano-1H-indole, 0.60 g of paraformaldehyde and 0.1 g of triethylamine was stirred at 130 ° C. for 1 hour. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.69 g of 3-cyano-1H-indole-1-ylmethanol.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5214ddbf0dd0471986e0fcda6acb5713
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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