Benzenamine, 3-ethynyl- → N-(3-ethynylphenyl)-7-nitroquinazolin-4-amine

HRID 1968634Notes

Reaction equation

HRID 1968634 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:15]([C:17]1[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=1)#[CH:16]>C(O)(C)C>[C:15]([C:17]1[CH:18]=[C:19]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:20]=[CH:21][CH:22]=1)#[CH:16]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 8306804-Chloro-7-nitroquinazoline

Product 1

HCID 16045519N-(3-ethynylphenyl)-7-nitroquinazolin-4-amineYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-7-nitroquinazoline (2.0 g, 9.54 mmol), isopropanol (30 mL), and 3-ethynylbenzenamine (1.2 g, 10.00 mmol) was refluxed for 5 h. The reaction mixture was cooled to room temperature and refrigerated. The solid was filtered, washed with cold isopropanol several times, and dried in vacuo to give 2.6 g (94%) of N-(3-ethynylphenyl)-7-nitroquinazolin-4-amine as a yellow solid.

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationThe solid was filtered
  3. washwashed with cold isopropanol several times
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a5b0009a281841efb168911fedbead1b
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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