3,4-Diaminobenzoic acid → HCID 178490106, compound

HRID 2395414Notes

Reaction equation

HRID 2395414 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH:17]=O)=[CH:5][CH:4]=1.[NH2:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[NH2:34])[C:28]([OH:30])=[O:29]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([C:17]3[NH:34][C:33]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=4[N:24]=3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 692633,4-Diaminobenzoic acidHCID 18971780HCID 18971780, compound

Product 1

HCID 178490106HCID 178490106, compoundYield 35.2%

Procedure

3-(4-(4-Methoxyphenyl)-butoxy)-4-methoxybenzaldehyde (2.8 g) and 3,4-diaminobenzoic acid (1.4 g) were heated to about 120° C. over 1 hour. The resulting residue was chromatographed on a 5×10 cm pad of silica gel eluting with ether to give 1.4 g of a beige solid which was recrystallized from 20 ml of methanol. M.P. 167°-169° C. MS m/e 450 (M+ +1). Elemental analysis calculated for C26H28 O5N2 : C, 69.62; H, 6.29; N, 6.24. Found: C, 69.72; H. 6.70; N, 5.75.

Workup

  1. customThe resulting residue was chromatographed on a 5×10 cm pad of silica gel eluting with ether

Sources & evidence

ORD record
ord-abb8d8132c83440f8f49e8af49a4bfd6
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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