Hydrochloric Acid → N-Acetyl-3-hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic Acid

HRID 1361010Notes

Reaction equation

HRID 1361010 reaction equation
[OH:1][C:2]1[C:3]([C:23]([OH:25])=[O:24])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH2:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[CH:6]=2.C(=O)([O-])O.[Na+].[C:31](OC(=O)C)(=[O:33])[CH3:32].Cl>O1CCCC1.O>[C:31]([N:13]([CH2:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([OH:1])[C:3]([C:23]([OH:25])=[O:24])=[CH:4]2)=[CH:9][CH:8]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 574897533-Hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic Acid

Product 1

HCID 59122790N-Acetyl-3-hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic AcidYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-7-[(4-(2-propyl)phenylamino)methyl]naphthalene-2-carboxylic acid (25 mg, 0.07 mmol) (example 363) was suspended in tetrahydrofuran (200 μL). A solution of sodium hydrogencarbonate (23 mg, 0.27 mmol) in water (200 μL) was added followed by acetic anhydride (14 μL, 15 mg, 0.15 mmol). The reaction mixture was stirred vigorously for 65 hours at room temperature before 6 N hydrochloric acid (4 mL) was added. The precipitate was filtered off and rinsed with water (3×1 mL) to yield the title compound (21 mg). No further purification was necessary.

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered off
  3. washrinsed with water (3×1 mL)

Sources & evidence

ORD record
ord-04fe33d6c0b94061bf524f7cecadb7cc
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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