2,4-Dichloro-5-methoxyaniline → HCID 25013536, compound

HRID 902430Notes

Reaction equation

HRID 902430 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:24]#[N:25])[C:15]([N:19]=[CH:20][N:21](C)C)=[CH:16]2)=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:28][C:29]1[CH:35]=[C:34]([Cl:36])[C:33]([O:37][CH3:38])=[CH:32][C:30]=1N>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:26][CH3:27])=[CH:11][C:12]2[CH:13]=[C:14]3[C:15](=[CH:16][C:17]=2[CH:18]=1)[N:19]=[CH:20][N:21]=[C:24]3[NH:25][C:30]1[CH:32]=[C:33]([O:37][CH3:38])[C:34]([Cl:36])=[CH:35][C:29]=1[Cl:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 69267448HCID 69267448, compound

Product 1

HCID 25013536HCID 25013536, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N′-(7-benzyloxy-3-cyano-6-methoxynaphthalen-2-yl)-N,N-dimethylformamidine and 0.092 g (0.48 mmol) of 2,4-dichloro-5-methoxyaniline in 4 mL of glacial acetic acid is heated under reflux for 7 hours, then cooled to room temperature and stirred overnight. The resulting solid is collected by filtration, washed with ether and dried to yield 0.05 g of (8-benzyloxy-7-methoxybenzo[g]quinazolin-4-yl)-(2,4-dichloro-5-methoxyphenyl)amine as a yellow solid, mp 275-280° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 7 hours
  3. filtrationThe resulting solid is collected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-79d0a44033984cbbad0c37543d6ba311
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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