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

Participants

Role	Name	HCID	Charge
Reactant	Methyl chloroformate	HCID 6586	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	8-hydrazino-3,4-dihydro-2,5-dimethyl-2H-1-benzopyran	HCID 13560298	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-(3,4-dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)hydrazinecarboxylic acid	HCID 20255573	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

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.

Provenance & Evidence

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