Ammonia → 4-Amino-6-methoxy-2-(3-methoxyphenyl)quinoline

HRID 716835Notes

Reaction equation

HRID 716835 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:7]=[C:6]2Cl.C1(O)C=CC=CC=1.[NH3:29]>>[NH2:29][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 996PhenolHCID 692378696-Methoxy-2-(3-methoxyphenyl)-4-chloroquinoline

Product 1

HCID 692397584-Amino-6-methoxy-2-(3-methoxyphenyl)quinoline

Conditions

Temperature
180 °C

Procedure

A mixture of 6-methoxy-2-(3-methoxyphenyl)-4-chloroquinoline (5.90 g, 19.68 mmol) and phenol (20 g) was heated with stirring at 180° C. and ammonia was passed through the reaction mixture during 11 h. Phenol was then removed by steam distillation. The mixture was filtered and the filtrate was basified to pH 8 by adding 8% Na2CO3 aqueous solution. The solid formed was collected by filtration and dried to give the desired 4-amino-6-methoxy-2-(3-methoxyphenyl)quinoline, 5.313 g (96.3%); mp 148-149° C.; 1H NMR (DMSO-d6) δ 3.85, 3.90 (each: 3H, s, OCH3), 6.67 (2H, s, exchangeable, NH2), 7.00 (1H, dd, J=2.9 and 8.1 Hz, ArH), 7.10 (1H, s, ArH), 7.28 (1H, dd, J=2.9 and 8.8 Hz, ArH), 7.40 (1H, t, J=8.1 Hz, ArH), 7.53 (1H, d, J=2.9 Hz, ArH), 7.61 (1H, 1H, d, J=8.1 Hz, ArH), 7.64 (1H, t, J=2.2 Hz, ArH), 7.77 (1H, d, J=8.8 Hz, ArH). Anal. Calcd. for (C17H16N2O2): C, 72.84; H, 5.75; N, 9.99. Found: C, 72.82; H, 5.51; N, 10.12.

Workup

  1. temperaturewas heated
  2. customPhenol was then removed by steam distillation
  3. filtrationThe mixture was filtered
  4. additionby adding 8% Na2CO3 aqueous solution
  5. customThe solid formed
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2c4df6d9465b47f687b56d77c1fc7aad
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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