Formaldehyde → 3-(Hydroxymethyl)imidazo[1,2-a]pyridine-6-carbonitrile

HRID 876831Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=12.[C:12]([O-])(=[O:14])C.[Na+].C=O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[OH:14][CH2:12][C:3]1[N:4]2[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of imidazo[1,2-a]pyridine-6-carbonitrile (7-1) (1.43 g, 10 mmol) in 3 mL of acetic acid were added sodium acetate (3.03 g, 37 mmol) and then formaldehyde (6 mL, 37% in water). The reaction mixture was stirred at 100° C. overnight. After cooled to room temperature, the mixture was adjusted to pH>7 with aqueous Na2CO3. The precipitate was collected to afford the title compound (1.4 g). MS (m/z): 174.0 (M+H)+

Workup

temperatureAfter cooled to room temperature
customThe precipitate was collected

Sources & evidence

ORD record: ord-1368d4636357420d8cb0669539725c8a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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