3-Chloro-4-methoxyaniline → (3-Chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-methyl-amine

HRID 1876220Notes

Reaction equation

HRID 1876220 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH2:22][Cl:23])[N:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[C:25]1C2C(=CC=CC=2)N=C(CCl)N=1.ClC1C=C(N)C=CC=1OC.Cl.ClCC1N=C(N(C2C=CC(OC)=CC=2)C)C2C(=CC=CC=2)N=1>Cl.CC(O)C>[Cl:2][C:3]1[CH:4]=[C:5]([N:11]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH2:22][Cl:23])[N:13]=2)[CH3:25])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 214413-Chloro-4-methoxyanilineHCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 68515345HCID 68515345, compoundHCID 68516138(3-Chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-amine hydrochloride

Product 1

HCID 59242090(3-Chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-methyl-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

(3-Chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-amine hydrochloride: The title compound was prepared from 4-chloro-2-chloromethyl-quinazoline (500 mg, 2.3 mmol), 3-chloro-4-methoxy-phenylamine (444 mg, 2.8 mmol) and HCl (12 M, 7 drops) in i-PrOH (8 mL) by a procedure similar to the preparation of (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride in Example 203c. 1H NMR (CDCl3) δ 8.6 (d, 1H), 8.1 (t, 1H), 7.85 (m, 3H), 7.62 (d, 1H), 7.20 (d, 1H), 4.8 (s, 2H), 3.92 (s, 3H); LC-MS (ESI+; 334 ([M+H]+)).

Sources & evidence

ORD record
ord-5c70b38631c7433cb03f0ad30e6168fe
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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