3-Amino-2-naphthoic acid → Methyl 3-aminonaphthalene-2-carboxylate

HRID 1095000Notes

Reaction equation

HRID 1095000 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:15]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][C:20]=1[NH2:31])[CH3:16].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.C(N(CC)CC)C>[CH3:15][O:13][C:12]([C:3]1[C:2]([NH2:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[O:14].[CH2:15]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][C:20]=1[NH2:31])[CH3:16]

Participants

8

Reactant 4

HCID 222443-Amino-2-naphthoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

Product 2

HCID 12471537Methyl 3-aminonaphthalene-2-carboxylateHCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-Amino-naphthalene-2-carboxylic acid (compound A′) (1.2 g) was dissolved in anhydrous methylene chloride (12 ml). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.5 g), 1-hydroxybenzotriazole monohydrate (1.5 g), and triethylamine (1 ml) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 3-amino-naphthalene-2-carboxylic acid methyl ester as a useful intermediate (compound A) (530 mg, yield 41%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-35c404e09c9941439e929202904fc318
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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