Ammonia → HCID 20571810, compound

HRID 1181432Notes

Reaction equation

HRID 1181432 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[NH3:14]>>[OH:1][CH2:2][CH2:3][C:4]1[N:14]=[CH:8][C:7]2[C:6]([CH:5]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 18944187HCID 18944187, compound

Product 1

HCID 20571810HCID 20571810, compoundYield 73.3%

Conditions

Temperature
80 °C

Procedure

A solution of 2-(4-hydroxybut-1-ynyl)benzaldehyde (Description 110; 8.50 g, 48.8 mmol) in 2M methanolic ammonia (122 ml, 244 mmol) contained in a Parr flask was heated at 80° C. for 2 hours (approx 35 psi achieved). The cooled mixture was evaporated and the residue purified by column chromatography on silica elution with a gradient rising from 1% MeOH in DCM+0.5% NH4OH to 5% MeOH in DCM+0.5% NH4OH to give the title compound (6.2 g, 73%) as a beige solid.

Workup

  1. customThe cooled mixture was evaporated
  2. customthe residue purified by column chromatography on silica elution with a gradient

Sources & evidence

ORD record
ord-b007f873201b4116b98ea5ed965092f9
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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