Aniline → HCID 68621065, compound

HRID 1182508Notes

Reaction equation

HRID 1182508 reaction equation
[CH3:1]/C(/CCCCC(C1C=CC2C(=CC=CC=2)C=1)=O)=C/C(O)=O.C1(N[C:30](=[O:51])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([C:39]2[CH:44]=[CH:43][C:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=CC=2)=[O:38])C=CC=CC=1.[C:52]1([NH2:59])[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[NH2:58].NC1C=CC=CC=1>>[NH2:58][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=1[NH:59][C:30](=[O:51])/[CH:31]=[C:32](/[CH3:1])\[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([C:39]1[C:46]2[C:45](=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:42]=[CH:43][CH:44]=1)=[O:38]

Participants

5

Reactant 4

HCID 6115AnilineHCID 7243O-PhenylenediamineHCID 23072397HCID 23072397, compoundHCID 68621190HCID 68621190, compound

Product 1

HCID 68621065HCID 68621065, compoundYield 99%

Procedure

Following a procedure described in Example 35, but substituting respectively acid 193 for acid 80 and 1,2-phenylenediamine for aniline, the compound 194 was obtained in 99% yield. 1H NMR: (300 MHz, CD3OD): 8.01 (d, 2H, J=8.0 Hz), 7.92 (d, 2H, J=8.8 Hz), 7.65-7.54 (m, 3H), 7.09 (d, J=8.0 Hz, 1H), 6.68 (dd, J=7.7, 7.4 Hz, 1H), 5.97 (s, 1H), 3.22 (t, J=7.1 Hz, 2H), 2.82 (dd, J=7.4, 7.7 Hz, 2H), 1.91-1.80 (m, 2H), 1.77-1.63 (m, 2H). 13C NMR: (75 MHz, CH3OD): 25.1, 25.2, 28.7, 33.4, 39.1, 118.6, 119.6, 124.7, 125.4, 126.9, 127.8, 127.9, 128.7, 129.4, 129.5, 130.7, 131.1, 133.9, 135.5, 136.9, 140.8, 143.0, 157.6, 167.5, 202.6

Sources & evidence

ORD record
ord-be561a8b43854c1abf94cda78f47f768
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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