Benzenamine, 3-ethynyl- → N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine

HRID 1968640Notes

Reaction equation

HRID 1968640 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]=[CH:13][N:14](C)C)#[N:2].N[C:18]1[CH:19]=[C:20]([C:24]#[CH:25])[CH:21]=[CH:22][CH:23]=1>CC(O)=O>[C:24]([C:20]1[CH:19]=[C:18]([NH:2][C:1]2[C:3]3[C:4](=[CH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=3)[N:12]=[CH:13][N:14]=2)[CH:23]=[CH:22][CH:21]=1)#[CH:25]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

Product 1

HCID 16045443N-(3-ethynylphenyl)-6-nitroquinazolin-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine (1.00 g, 4.58 mmol) and 3-aminophenylacetylene (0.64 g, 5.49 mmol) in HOAc (15 mL) was stirred at 100° C. for 3 h and cooled to room temperature. The precipitate was filtered, washed with ether, and was dried in vacuo to give 1.23 g (93%) of N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with ether
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-4562643278c1410c984b78e43112c2ef
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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