Ammonia → 8-(4-(3-Anilinophenoxy)-1-methylbutoxy)quinolin-2-amine

HRID 1611689Notes

Reaction equation

[NH:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19](OC)=O.[NH3:26]>>[NH:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][CH2:12][CH2:13][CH2:8][CH:9]([CH3:10])[O:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:18]2[C:17]=1[N:26]=[C:2]([NH2:1])[CH:3]=[CH:19]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 75463-Hydroxy-N-phenylaniline

HCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 100703478-(4-(3-Anilinophenoxy)-1-methylbutoxy)quinolin-2-amine

Procedure

The title compound was prepared according to the procedure described in Example 92 substituting 3-anilinophenol for methyl 3-hydroxybenzoate. 1H NMR (500 MHz, CDCl3) δ ppm 7.91 (d, 1H), 7.26 (m, 3H), 7.16 (m, 1H), 7.12 (m, 1H), 7.07 (m, 3H), 6.94 (d, 1H), 6.91 (m, 1H), 6.60 (m, 1H), 6.52 (t, 1H), 6.37 (m, 1H), 4.69 (m, 1H), 4.03 (m, 1H), 3.96 (m, 1H), 2.18 (m, 1H), 1.96 (m, 3H), 1.46 (d, 3H); MS (DCI/NH3) m/z 414 [M+H]+.

Sources & evidence

ORD record: ord-eecabcd3960d48c794ad8350cd4139cf
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989392B2

Reaction notes

Loading…