Methanol → HCID 69794861, compound

HRID 2181664Notes

Reaction equation

HRID 2181664 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8][C:6]=2[CH:7]=1)#[N:2].C[OH:17]>O>[NH2:2][C:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:6]=2[CH:7]=1)=[O:17]

Participants

4

Reactant 2

HCID 887MethanolHCID 22481677HCID 22481677, compound

Product 1

HCID 69794861HCID 69794861, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-cyano-1-benzofuran-5-carboxylate (426 mg, 2.0 mmol) is dissolved in MeOH (10 ml). The solution is cooled to 0° C., is treated with LiOH monohydrate (168 mg, 4.0 mmol) in H2O (4 ml), and the reaction is stirred 6 h at RT. The volatiles are removed in vacuo and the residue is dissolved in H2O (10 ml). The pH of the mixture is adjusted to 1.9 with 12N HCl, the white solid is collected, washed with water, and is dried to give 401 mg (97%) of 2-(aminocarbonyl)-1-benzofuran-5-carboxylic acid as an off-white solid. MS (EI) calcd for C10H7NO4: 205.0375, found 205.0369 (M)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in H2O (10 ml)
  3. customthe white solid is collected
  4. washwashed with water
  5. customis dried

Sources & evidence

ORD record
ord-36f09ea7e7d047e1871b80e494319381
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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