3-Amino-4-hydroxybenzoic acid → HCID 24782628, compound

HRID 2422948Notes

Reaction equation

HRID 2422948 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([C:26](O)=[O:27])[CH:20]=[CH:19]2)=[O:15]>C(Cl)Cl.N1C=CC=CC=1>[OH:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:26]([C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([C:14]([O:13][CH3:12])=[O:15])[CH:17]=2)[CH:22]=1)=[O:27]

Participants

5

Reactant 2

HCID 650833-Amino-4-hydroxybenzoic acidHCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acid

Product 1

HCID 24782628HCID 24782628, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-amino-4-hydroxybenzoic acid (0.142 g, 0.927 mmol) and the acyl chloride prepared from acid 74 (in 84% yield) (0.259 g, 1.019 mmol) in DCM (5 ml) and pyridine (6 ml) was stirred at room temperature for under at for 24 h. The solvent was removed under reduced pressure. HCl (aq, 4 M, 6 ml) was added and the precipitate was filtered, washed with water (10 ml) and dried under vacuum. Trituration with methanol (15 ml) and acetone (10 ml) afforded 75 as an off-white solid (0.084 g, 0.230 mml, 25%). 1H NMR (400 MHz, DMSO-d6) δ 3.92 (3H, s), 7.00 (1H, d, J 8.4 Hz), 7.67 (1H, d, J 8.8 Hz), 8.04-8.10 (2H, m), 8.16-8.27 (2H, m), 8.33 (1H, s), 8.70-8.66 (2H, m), 9.80 (1H, s), 10.55 (1H, bs). 13C NMR (100 MHz, DMSO-d6) δ 53.09, 116.18, 122.59, 125.94, 126.45, 126.26, 126.80, 128.45, 128.48, 129.19, 130.35, 130.40, 130.93, 134.13, 134.66, 134.94, 154.61, 165.85, 166.84, 167.73. νmax (solid)/(cm−1) 3059, 1716, 1666, 1592, 1541, 1283, 1247, 1132, 759.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionHCl (aq, 4 M, 6 ml) was added
  3. filtrationthe precipitate was filtered
  4. washwashed with water (10 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-80da2135116e49489ccfd49ae6965a94
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

Loading…