Ethanol → 2-[4-(Aminomethyl)phenyl]quinazoline-4-carboxylic acid

HRID 717341Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:28]=[C:27]([C:29]([O:31]CC)=[O:30])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1.C(O)C.[OH-].[K+]>C(O)(=O)C>[NH2:3][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 500-mL round-bottom flask, was placed ethyl 2-[4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phenyl]quinazoline-4-carboxylate (4 g, 9.14 mmol, 1.00 equiv), ethanol (40 mL) and 1N KOH (70 mL). The resulting solution was stirred for 24 h at 100° C. in an oil bath. The pH value of the solution was adjusted to 7 with acetic acid. The resulting mixture was concentrated under vacuum. This resulted in 2.6 g (crude) of 2-[4-(aminomethyl)phenyl]quinazoline-4-carboxylic acid as a white solid. MS (ESI) m/z 280 ([M+H]+).

Workup

customInto a 500-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 2.6 g (crude) of 2-[4-(aminomethyl)phenyl]quinazoline-4-carboxylic acid as a white solid

Sources & evidence

ORD record: ord-17749f26da15416785f7bedda0dc6e2d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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