4-Aminophenol → HCID 118372883, compound

HRID 2282069Notes

Reaction equation

HRID 2282069 reaction equation
[C:1]([C:3]1[C:27](F)=[CH:26][CH:25]=[CH:24][C:4]=1[O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17](F)[C:16]=2[C:22]#[N:23])[C:7]=1[C:8]#[N:9])#[N:2].[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.[C:37](=[O:40])([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:17]2[C:16]([C:22]#[N:23])=[C:15]([CH:20]=[CH:19][CH:18]=2)[O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:6]([O:5][C:4]3[CH:24]=[CH:25][CH:26]=[C:27]([O:40][C:37]4[CH:34]=[CH:35][C:30]([NH2:29])=[CH:31][CH:32]=4)[C:3]=3[C:1]#[N:2])[C:7]=2[C:8]#[N:9])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 118372882HCID 118372882, compound

Product 1

HCID 118372883HCID 118372883, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,6-bis[3-(4-aminophenoxy)-2-cyanophenoxy]benzonitrile (p,p-3CN; 6b in FIG. 1) was prepared from 2,6-bis(2-cyano-3-fluorophenoxy)benzonitrile (2.00 g, 5.4 mmol), 4-aminophenol (1.29 g, 11.8 mmol), potassium carbonate (1.78 g, 12.9 mmol), and NMP (32 mL) using the same procedure as Example 3 to obtain 1.52 g (51.5%) of beige solid, m.p. 242.6-243.8° C. (dec.). 1H-NMR (DMSO-d6): 5.18 (s, 4H, Ar—H), 6.57-6.65 (m, 6H, Ar—H), 6.88-6.92 (m, 2H, Ar—H), 7.58-7.61 (t, 2H, Ar—H), 7.77-7.80 (t, 1H, Ar—H). Elemental analysis: Calcd.: C, 71.86; H, 3.84; N, 12.70. Found: C, 71.40; H, 4.00; N, 12.33.

Sources & evidence

ORD record
ord-ea3b04cf92b64f5b886bf9f57f4e2e82
Source dataset
uspto-grants-2015_09
Patent number
US09139696B1

Reaction notes

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