6-(Dimethoxymethyl)-2-hydroxynicotinic acid

Base Information

• Chemical Name: 6-(Dimethoxymethyl)-2-hydroxynicotinic acid
• CAS No.: 156459-20-0
• Molecular Formula: C9H11NO5
• Molecular Weight: 213.18734
• Hs Code.: 2933399990
• European Community (EC) Number: 871-519-5
• DSSTox Substance ID: DTXSID401174402
• Mol file: 156459-20-0.mol

Synonyms:156459-20-0;6-(DIMETHOXYMETHYL)-2-HYDROXYNICOTINIC ACID;6-(Dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid;6-(dimethoxymethyl)-2-oxo-1H-pyridine-3-carboxylic Acid;2-hydroxy-6-(dimethoxymethyl)pyridine-3-carboxylic acid;SCHEMBL21798220;DTXSID401174402;AMY37294;3-Pyridinecarboxylic acid, 6-(dimethoxymethyl)-1,2-dihydro-2-oxo-;MFCD12974278;AKOS027426496;CS-W000312;AS-47814;BP-11741;EN300-399302;F16232;6-(DIMETHOXYMETHYL)-2-HYDROXYNICOTINICACID;Z1508931933;6-(DIMETHOXYMETHYL)-2-HYDROXYPYRIDINE-3-CARBOXYLIC ACID;6-(dimethoxymethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Chemical Property of 6-(Dimethoxymethyl)-2-hydroxynicotinic acid

Chemical Property:

• Melting Point: 173 - 175 °C
• Boiling Point: 413.7±45.0 °C(Predicted)
• PKA: 2.37±0.20(Predicted)
• PSA: 88.62000
• Density: 1.343±0.06 g/cm3(Predicted)
• LogP: 0.36450
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 340

Purity/Quality:

98%min ^*data from raw suppliers

6-(dimethoxymethyl)-2-hydroxynicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(C1=CC=C(C(=O)N1)C(=O)O)OC

Technology Process of 6-(Dimethoxymethyl)-2-hydroxynicotinic acid

There total 2 articles about 6-(Dimethoxymethyl)-2-hydroxynicotinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

3-cyano-6-(dimethoxymethyl)-2-pyridone (156459-19-7) → 6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0)

Guidance literature:

With potassium hydroxide; for 25h; Heating;

DOI:10.1002/jhet.5570310207

Reference yield:

Pyruvic aldehyde dimethyl acetal (6342-56-9) → 6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methoxide / tetrahydrofuran / 3.5 h / 45 °C

2: H⁺ / H₂O / 16 h / 60 °C

3: 82 percent / aq. KOH / 25 h / Heating

With potassium hydroxide; sodium methylate; hydrogen cation; In tetrahydrofuran; water;

DOI:10.1002/jhet.5570310207

Reference yield:

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0) → (R)-2'-[5-Benzyloxycarbonyl-6-((R)-1-tert-butoxycarbonylamino-ethyl)-pyridin-2-yl]-4,5-dihydro-[2,4']bithiazolyl-4-carboxylic acid (348128-89-2)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 7.73 mg / p-toluenesulfonic acid hydrate / Heating

2.1: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

3.1: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

4.1: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

5.1: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

6.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

7.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

8.1: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

9.1: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

10.1: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

11.1: 2M HCl / tetrahydrofuran / 20 °C

12.1: Et₃N / toluene / 10 h / 0 °C

12.2: 1.91 g / MnO₂ / toluene / 20 °C

13.1: 1M LiOH / H₂O; dioxane / 5 h / 0 - 20 °C

14.1: 83 percent / Et₃N / dimethylformamide / 6 h / 0 - 20 °C

15.1: 77 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

16.1: 83 percent / Jones reagent / acetone / 0.67 h / 0 °C

17.1: K₂CO₃ / H₂O; tetrahydrofuran / 8.5 h / 0 - 20 °C

18.1: 0.47 g / Et₃N; DPPA / dimethylformamide / 0 - 20 °C

19.1: 1M LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 - 20 °C

20.1: 2.03 g / Et₃N / dimethylformamide / 12.5 h / 0 - 20 °C

21.1: 68 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 12 h / 50 °C

22.1: 41 percent / 2M HCl / tetrahydrofuran / 20 °C

23.1: 69 percent / Ph₃P; DEAD / tetrahydrofuran; toluene / 0.5 h / 0 °C

24.1: TFA / CHCl₃ / 5 h / 20 °C

25.1: Et₃N / CHCl₃ / 5.5 h / 0 - 20 °C

With Lawessons reagent; hydrogenchloride; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; sodium azide; jones reagent; diphenyl-phosphinic acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; calcium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; 23.1: Mitsunobu reaction;

DOI:10.1246/bcsj.75.1583

upstream raw materials:

3-cyano-6-(dimethoxymethyl)-2-pyridone

Pyruvic aldehyde dimethyl acetal

Downstream raw materials:

6-formyl-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid

(RS)-3-(t-butyldiphenylsiloxymethyl)-6-dimethoxymethyl-2-(1-hydroxyethyl)pyridine

1-[3-(tert-butyl-diphenyl-silanyloxymethyl)-6-dimethoxymethyl-pyridin-2-yl]-ethylamine

(RS)-2-(1-azidoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine