O-Phenylenediamine → HCID 58982145, compound

HRID 1182480Notes

Reaction equation

HRID 1182480 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].[NH2:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26].[C:31]1(N)C=CC=C[C:32]=1N>>[NH2:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][NH:26][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:1]=[CH:10][C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:32][CH:31]=2)=[CH:4][CH:3]=1)=[O:12]

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 1780962-(Aminomethyl)anilineHCID 109459918-(2-NAPHTHYL)-8-OXOOCTANOIC ACID

Product 1

HCID 58982145HCID 58982145, compoundYield 32%

Procedure

Following the procedure described in Example 22, but substituting carboxylic acid 50h for carboxylic acid 50g and 2-aminobenzylamine for 1,2-phenylenediamine respectively, the title compound 75 was obtained in 32% yield. 1H NMR (300 MHz, CDCl3): δ 8.02 (d, J=8.4 Hz, 2H), 7.71-7.61 (m, 4H), 7.37-7.51 (m, 3H), 7.12-7.01 (m, 2H), 6.70-6.62 (m, 2H), 5.76 (br s, 1H), 4.38 (d, J=6.3 Hz, 2H), 2.97 (t, J=7.5 Hz, 2H), 2.19 (t, J=7.5 Hz, 2H), 1.80-1.58 (m, 4H), 1.45-1.32 (m, 4H).

Sources & evidence

ORD record
ord-7eac6e59370f4edb98237fc3a0939d8b
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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