Aniline → HCID 68998282, compound

HRID 1182509Notes

Reaction equation

HRID 1182509 reaction equation
C1(N[C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=CC=2)=[O:16])C=CC=CC=1.[C:30]1([NH2:37])[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36].N[C:39]1C=CC=CC=1>>[NH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:37][C:8](=[O:29])[CH2:9][CH:10]([CH3:39])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:17]1[C:24]2[C:23](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1)=[O:16]

Participants

4

Reactant 3

HCID 6115AnilineHCID 7243O-PhenylenediamineHCID 68621190HCID 68621190, compound

Product 1

HCID 68998282HCID 68998282, compoundYield 87%

Procedure

Following a procedure described in Example 35, but substituting acid 193 for acid 80 1,2-phenylenediamine for aniline, the compound 198 was obtained in 87% yield. 1H NMR: (300 MHz, CD3OD): 8.05-7.91 (m, 4H), 7.67-7.53 (m, 2H), 7.10-6.68 (m, 5H), 3.33-3.31 (m, 2H), 3.19 (dd, J=6.9, 7.4 Hz, 2H), 2.47-1.29 (m, 7H), 1.05 (d, J=6.6 Hz, 3H), 13C NMR (75 MHz, CD3OD): 20.1, 25.8, 27.7, 32.1, 37.7, 39.4, 44.87, 118.6, 119.5, 124.7, 127.1, 127.8, 128.3, 128.8, 129.5, 129.6, 130.7, 131.1, 134.1, 137.1, 174.6, 202.7.

Sources & evidence

ORD record
ord-84b7ba6832834a30a525de3e86e06e34
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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