Triethylamine → HCID 18184418, compound

HRID 1489576Notes

Reaction equation

HRID 1489576 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].CCN(CC)CC>COC(O)C>[ClH:1].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115623-BromoanilineHCID 110638054-chlorobenzo[g]quinazoline

Product 1

HCID 18184418HCID 18184418, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

4-Chlorobenzo[g]quinazoline (214 mg, 1.0 mmol), 3-bromoaniline (213 mg, 1.25 mmol) and NEt3 (202 mg, 2.0 mmol) in stirred methoxyethanol (5 mL) were heated under N2 at 95° C. for 6 h. The volatiles were removed under reduced pressure and the residual solid was triturated with MeOH. The solid was recrystallized at 0° C. from an EtOH/dilute hydrochloric acid mixture (1:4, 0.05M acid, 50 mL) after celite filtration to give 4-(3-bromoanilino)-benzo[g]quinazoline hydrochloride (71 mg, 18%) as a yellow-green solid. 1H NMR (DMSO) δ14.0 (1H brs), 9.65 (1H, s), 9.01 (1H, s), 8.47 (1H, s), 8.29 (1H, d, J=8.4 Hz), 8.24 (1H, d, J=8.4 Hz), 8.18 (1H, slbrs), 7.9-7.82 (2H, m), 7.78 (1H, t, J=7.5 Hz), 7.58 (1H, d, J=8 Hz), 7.51 (1H, t, J=8 Hz). ##STR21##

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residual solid was triturated with MeOH
  3. customThe solid was recrystallized at 0° C. from an EtOH/dilute hydrochloric acid mixture (1:4, 0.05M acid, 50 mL)
  4. filtrationafter celite filtration

Sources & evidence

ORD record
ord-c816456518484e3eb3171639ab6fc2c0
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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