Sodium Hydroxide → HCID 90411025, compound

HRID 717334Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 2-(4-nitrophenyl)quinazoline-4-carboxylate (1.2 g, 3.71 mmol, 1.00 equiv), water (13 mL), sodium hydroxide (150 mg, 3.75 mmol, 2.00 equiv) and sodium hyposulfite (1.3 g, 2.00 equiv). The resulting solution was stirred for 12 h at 80° C. in an oil bath. The solids were filtered out. The filter cake was washed with 1×50 mL of ethanol. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 0.8 g (73%) of ethyl 2-(4-aminophenyl)quinazoline-4-carboxylate as a yellow solid. MS (ESI) m/z 294 ([M+H]+).

Workup

customInto a 100-mL 3-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
filtrationThe solids were filtered out
washThe filter cake was washed with 1×50 mL of ethanol
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 0.8 g (73%) of ethyl 2-(4-aminophenyl)quinazoline-4-carboxylate as a yellow solid

Sources & evidence

ORD record: ord-f204bb85c0b04e0d8f9e01b989ce3165
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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