Formamide → 7-(Hydroxymethyl)quinazolin-4(1H)-one

HRID 1433105Notes

Reaction equation

HRID 1433105 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH:14]([NH2:16])=O>>[OH:13][CH2:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:5])[NH:16][CH:14]=[N:1]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 602338Methyl 2-amino-4-(hydroxymethyl)benzoate

Product 1

HCID 1357422347-(Hydroxymethyl)quinazolin-4(1H)-one

Conditions

Temperature
180 °C

Procedure

A mixture of 2.0 g (19.1 mmole) of methyl 2-amino-4-hydroxymethlybenzoate in 4 ml of formamide is heated in an oil bath of 180° C. for three hours. The mixture is cooled and triturated with 70 ml of boiling ethyl acetate. The ethyl acetate is then decanted from the dark oil and cooled in a freezer overnight to precipitate 0.7 g 205-12° C. mp; 40% yield. 1H NMR (d6-DMSO, 300 MHz) δ 8.08 (s, 1H), 8.06 (d, 1H), 7.60 (s, 1H), 7.45 (d, 1H), 5.48 (bs, 1H), 4.65 (s, 2H), 3.35 (bs, 1H). EI MS, [M]+=176.

Workup

  1. temperatureThe mixture is cooled
  2. customtriturated with 70 ml of boiling ethyl acetate
  3. customThe ethyl acetate is then decanted from the dark oil
  4. temperaturecooled in a freezer overnight
  5. customto precipitate 0.7 g 205-12° C. mp; 40% yield

Sources & evidence

ORD record
ord-6468761fdf724be78369cdc753bd62c5
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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