Sodium Hydroxide → 8-[2-(Benzyloxymethyl)chromane-6-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 1603878Notes

Reaction equation

HRID 1603878 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([NH:22][C:23]3[C:32]4[O:31][C:30]([C:33]([O:35]CC)=[O:34])=[CH:29][C:28](=[O:38])[C:27]=4[CH:26]=[CH:25][CH:24]=3)=[O:21])[CH:16]=2)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([NH:22][C:23]3[C:32]4[O:31][C:30]([C:33]([OH:35])=[O:34])=[CH:29][C:28](=[O:38])[C:27]=4[CH:26]=[CH:25][CH:24]=3)=[O:21])[CH:16]=2)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19606281Ethyl 8-[2-(benzyloxymethyl)chromane-6-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylate

Product 1

HCID 196063368-[2-(Benzyloxymethyl)chromane-6-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 8-[2-(benzyloxymethyl)chromane-6-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylate (0.240 g, 0.47 mmol) in a mixture of methanol (15 ml) and tetrahydrofuran (15 ml) was added with 0.510 ml of a 1M NaOH solution, stirring at room temperature for 1.30 h. After that the mixture was evaporated to dryness and the resulting residue was suspended in water adding 0.2M hydrochloric acid to slightly acid pH (pH=4-5). The solid was recovered by filtration, washed with methanol and dried on phosphorous pentoxyde under vacuum, thereby obtaining 0.221 g of the title compound as a white solid which decomposes above 283° C. (97% yield).

Workup

  1. customAfter that the mixture was evaporated to dryness
  2. filtrationThe solid was recovered by filtration
  3. washwashed with methanol
  4. customdried on phosphorous pentoxyde under vacuum

Sources & evidence

ORD record
ord-84f6047b08b24789b0df33ef750b002f
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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