Methyl chloroformate → 2-(3,4-dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)hydrazinecarboxylic acid

HRID 637631Notes

Reaction equation

[NH:1]([C:3]1[C:12]2[O:11][CH:10]([CH3:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH3:14])=[CH:5][CH:4]=1)[NH2:2].C(N(C(C)C)CC)(C)C.Cl[C:25]([O:27]C)=[O:26]>C1COCC1>[CH3:13][CH:10]1[CH2:9][CH2:8][C:7]2[C:6]([CH3:14])=[CH:5][CH:4]=[C:3]([NH:1][NH:2][C:25]([OH:27])=[O:26])[C:12]=2[O:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of the 1F, 200 ml of THF and 12.4 g of N,N-diisopropyl-N-ethylamine was chilled to 0° C. and 9.1 g of methyl chloroformate was added, drop-by-drop, over five minutes. The mixture was poured over ice water and extracted with ether. The extract was dried (MgSO4) and concentrated to dryness, to give the methyl ester of 2-(3,4-dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)hydrazinecarboxylic acid (1G), as an amber syrup.

Workup

extractionextracted with ether
dry with materialThe extract was dried (MgSO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-a6f1e557de6d4f1abd65b87178e1f911
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04558040

Reaction notes

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