Methanol → HCID 10465243, compound

HRID 1583249Notes

Reaction equation

HRID 1583249 reaction equation
[OH2:1].[OH-:2].[Li+].CO[C:6](=O)[C:7]1[CH:16]=[C:15]([NH2:17])[CH:14]=[C:9]([C:10]([O:12]C)=[O:11])[CH:8]=1.[CH3:19]O>O>[NH2:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([CH2:6][C:19]([OH:2])=[O:1])[CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 66831Dimethyl 5-aminoisophthalateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 10465243HCID 10465243, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One equivalent of lithium hydroxide monohydrate was added to a solution of dimethyl-5-aminoisophthalate (prepared from 5-aminoisophthalic acid, thionyl chloride and methanol) in methanol (75 ml) and water (20 ml) and stirred at room temperature for 24 hours. The cloudy solution was heated for 2 hours on a hot plate and stripped of methanol on a rotary evaporator. The residue was triturated with hydrochloric acid and then extracted into methylene chloride (2×75 ml). The combined methylene chloride extracts were dried over sodium sulfate, filtered and stripped of solvent. The material was purified by crystallization from methanol-ethyl ether. m.p. 214°-220° C.

Workup

  1. temperatureThe cloudy solution was heated for 2 hours on a hot plate
  2. customstripped of methanol on a rotary evaporator
  3. customThe residue was triturated with hydrochloric acid
  4. extractionextracted into methylene chloride (2×75 ml)
  5. dry with materialThe combined methylene chloride extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customThe material was purified by crystallization from methanol-ethyl ether

Sources & evidence

ORD record
ord-3e6c3db0508e4e238f406a564ae6c787
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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