5-Aminovaleric acid → HCID 18411557, compound

HRID 992232Notes

Reaction equation

HRID 992232 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 1385-Aminovaleric acidHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 18411557HCID 18411557, compoundYield 98%

Procedure

4-nitrophthalic anhydride (0.25 g, 0.0013 mol) and 5-aminopentanoic acid (0.152 g, 0.0013 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.37 g (98%) 143 as dull white crystals: mp=172° C.; Rf0.93 (A): Rf0.83 (B): Rf0.69 (D): 1H NMR (DMSO-d6) δ1.83 (m, 2H), 2.29 (t, J=7.2 Hz, 2H), 3.64 (t, J=6.7 Hz, 2H), 8.01 (d, J=7.6 Hz, 1H), 8.45 (d, J=1.9 Hz, 1H), 8.59 (dd, J=7.6, 1.9 Hz, 1H); IR (cm−1): 2750-3200 (OH), 3056 (C═CH), 2620 (C—H), 1773 (C═O), 1707 (bs, C═O), 1624 (C═C), 1543 (N═O), 1438 (C═C), 1403 (C—O), 1351 (N═O), 1217 (C—O), 1068 (C—O), 723 (C═CH); MS m/z (rel intensity) 305 (100).

Workup

  1. customThe clear solution was purified as per 120

Sources & evidence

ORD record
ord-7a837771611c4ba8b7db2a623a1b89d9
Source dataset
uspto-grants-2002_10
Patent number
US06468990B1

Reaction notes

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