Acetic Acid → 3-Hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic Acid

HRID 1361009Notes

Reaction equation

HRID 1361009 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([OH:16])[C:9]([C:13]([OH:15])=[O:14])=[CH:10]2)=[CH:5][CH:4]=1)=O.C(O)(=O)C.[CH3:21][CH:22]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[CH3:23].C([BH3-])#N.[Na+].Cl>CO>[OH:16][C:8]1[C:9]([C:13]([OH:15])=[O:14])=[CH:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([CH2:1][NH:28][C:27]1[CH:29]=[CH:30][C:24]([CH:22]([CH3:23])[CH3:21])=[CH:25][CH:26]=1)[CH:12]=2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 74644-IsopropylanilineHCID 5003444Sodium cyanoborohydrideHCID 574570407-Formyl-3-hydroxy-2-naphthoic acid

Product 1

HCID 574897533-Hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic AcidYield 62.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Formyl-3-hydroxynaphthalene-2-carboxylic acid (40 mg, 0.19 mmol) (example 342) was suspended in methanol (300 μL). Acetic acid (16 μL, 17 mg, 0.28 mmol) and 4-(2-propyl)aniline (40 μL, 40 mg, 0.30 mmol) were added consecutively, and the resulting mixture was stirred vigorously at room temperature for 2 hours. Sodium cyanoborohydride (1.0 M in tetrahydrofuran, 300 μL, 0.3 mmol) was added, and the stirring was continued for another 17 hours. The reaction mixture was poured into 6 N hydrochloric acid (aq.) (6 mL), and the precipitate was filtered off and rinsed with water (3×2 mL) to yield the title compound (40 mg) as its hydrochloride salt. No further purification was necessary.

Workup

  1. waitthe stirring was continued for another 17 hours
  2. filtrationthe precipitate was filtered off
  3. washrinsed with water (3×2 mL)

Sources & evidence

ORD record
ord-e803741bc3df40f7bf27e8325583280c
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

Loading…