1-Naphthaldehyde → 6-(Morpholino)-2-(naphthalen-1-yl)quinazolin-4-one

HRID 2167236Notes

Reaction equation

HRID 2167236 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:16])=[C:11]([CH:15]=2)[C:12]([NH2:14])=[O:13])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:17]1([CH:27]=O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>>[O:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:15]=[C:11]3[C:10](=[CH:9][CH:8]=2)[N:16]=[C:27]([C:17]2[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=2)[NH:14][C:12]3=[O:13])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 61951-NaphthaldehydeHCID 105609362-Amino-5-(morpholin-4-yl)benzamide

Product 1

HCID 1362721586-(Morpholino)-2-(naphthalen-1-yl)quinazolin-4-one

Procedure

Compound 29 was synthesized from 5-morpholinyl-2-aminobenzamide (13) (1.6 g, 7.3 mmol) and 1-naphthaldehyde (14) (1.1 g, 7.3 mmol): yield 1.7 g (64%); yellow crystals; mp 291 to 293° C.; 1H NMR (DMSO-d6) δ 3.22 (4H, t, J=4.7 Hz, CH2NCH2), 3.77 (4H, t, J=4.7 Hz, CH2OCH2), 7.51-7.66 (6H, m, 6×ArH), 7.73-7.76 (1H, m, 1×ArH), 8.00-8.11 (3H, m, 3×ArH), 12.48 (1H, br s, NH) ppm; MS (ESI) m/z 357; Anal. (C22H19N3O2): C, H, N.

Sources & evidence

ORD record
ord-03d6497501aa48e0b08761f6c4bf550f
Source dataset
uspto-grants-2015_06
Patent number
US09045437B2

Reaction notes

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