4-(aminomethyl)-N,N-dimethylaniline dihydrochloride → 5-({[4-(Dimethylamino)benzyl]amino}methyl)-6-methoxy-2-naphthoic acid

HRID 23232Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=2[CH:15]=O)[CH:6]=1)=[O:4].Cl.Cl.[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1>>[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][CH2:15][C:11]2[C:10]([O:17][CH3:18])=[CH:9][CH:8]=[C:7]3[C:12]=2[CH:13]=[CH:14][C:5]([C:3]([OH:2])=[O:4])=[CH:6]3)=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochloride

HCID 118068606-Methoxy-5-formyl-2-naphthoic acid methyl ester

Product 1

HCID 99760235-({[4-(Dimethylamino)benzyl]amino}methyl)-6-methoxy-2-naphthoic acid

Procedure

The title compound was prepared as a white solid (0.160 g, 23% for two steps) from 6-methoxy-5-formyl-2-naphthoic acid methyl ester using p-dimethylamino-benzyl amine dihydrochloride and a procedure similar to steps 3-4 of Example 1, mp >215° C. (decomp.); 1H NMR (DMSO-d6) δ2.97 (s, 6H), 3.94 (s, 3H), 4.14-4.23 (m, 2H), 4.39-4.48 (m, 2H), 6.88-7.14 (bs, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.59 (d, J=9.3 Hz, 1H), 7.97 (dd, J=1.7, 8.9 Hz, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.26 (d, J=9.2 Hz, 1H), 8.59 (d, J=1.6 Hz, 1H), 9.05-9.24 (bs, 2H), 11.90-13.75 (bs, 1H); IR (neat) 3320, 2330-3130, 1705, 1670, 1625, 1580, 1515, 1485, 1460, 1430, 1280, 1260, 1220, 1200, 1175, and 1100 cm−1; mass spectrum [(+) ESI], m/z 365 (M +H)+ and [(−) ESI], m/z 363 (M−H)−; Anal. Calcd. for C22H24N2O3. 2HCl.1.25H2O: C, 57.46; H, 6.25; N, 6.09, Found: C, 57.25; H, 6.37; N, 5.93.

Sources & evidence

ORD record: ord-fe2b22f292e04c958de1e0fd7d2a4bf8
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849761B2

Reaction notes

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