2-Chloro-4-methoxyaniline → HCID 86706294, compound

HRID 2205881Notes

Reaction equation

HRID 2205881 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:18]3[CH:19]=[N:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:22]=3)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]=2[CH:3]=1.[Cl:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:32]=1[NH2:39]>>[C:26]([O:25][C:23]([N:21]1[CH:22]=[C:18]([C:9]2[N:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[C:4]3[CH:3]=[C:2]([NH:39][C:32]4[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:31]=4[Cl:30])[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 4074322-Chloro-4-methoxyanilineHCID 86706270HCID 86706270, compound

Product 1

HCID 86706294HCID 86706294, compoundYield 72%

Procedure

The title compound was prepared in 72% yield from compound (10) and 2-chloro-4-methoxyphenylamine using the method described for Preparation 35. 1H-NMR (CDCl3, 500 MHz): δ 1.49 (s, 9H), 1.69 (s, 9H), 3.82 (s, 3H), 6.58 (d, J=0.95 Hz, 1H over br s, 1H), 6.86 (dd, J=2.84, 8.83 Hz, 1H), 7.03 (d, J=2.84 Hz, 1H), 7.38 (m, 1H), 7.73 (d, J=9.14 Hz, 1H), 7.82 (d, J=0.63 Hz, 1H), 8.21 (d, J=0.63 Hz, 1H), 8.46 (d, J=0.63 Hz, 1H).

Workup

  1. customdescribed for Preparation 35

Sources & evidence

ORD record
ord-05c633a54d704440be9ee678163d6ca5
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

Loading…