Hydrochloric Acid → HCID 14971256, compound

HRID 466169Notes

Reaction equation

HRID 466169 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15]([C:18](O)=[O:19])=[CH:14][C:13]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[CH3:34][NH:35][OH:36].C(N(CC)CC)C.Cl>ClCCl.C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15]([C:18]([N:35]([OH:36])[CH3:34])=[O:19])=[CH:14][C:13]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 21883527HCID 21883527, compound

Product 1

HCID 14971256HCID 14971256, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

6-Benzyloxy-2H-1-benzopyran-3-carboxylic acid (362 mg, 1.33 mmol) and DMF (97 mg, 1.33 mmol) are dissolved in 5 ml of dichloromethane. To this is added oxalyl chloride (0.38 g, 2.99 mmol) and the mixture is stirred until no further gas evolution is observed (2 hours). This acid chloride solution is slowly added to a mixture of N-methylhydroxylamine hydrochloride (0.44 g, 5.32 mmol) and triethylamine (0.81 g, 7.98 mmol) in THF/water (4.1 ml/0.99 ml). The resultant mixture is stirred at room temperature for 1 hour, and poured onto 100 ml of 2N aqueous HCl. The mixture is extracted twice with dichloromethane and the organic phase is dried (MgSO4). Evaporation followed by trituration of the residual solid with ethyl acetate/hexane gives 6-benzyloxy-N-hydroxy-N-methyl-2H-1-benzopyran-3-carboxamide, m.p. 143°-146° C., as a pale yellow solid.

Workup

  1. custom(2 hours)
  2. extractionThe mixture is extracted twice with dichloromethane
  3. dry with materialthe organic phase is dried (MgSO4)
  4. customEvaporation

Sources & evidence

ORD record
ord-f232c473e6954058926d43c9b91295a7
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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