Triethylamine → HCID 54324149, compound

HRID 364131Notes

Reaction equation

HRID 364131 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]=1.[Br:18]Br.C(N(CC)CC)C>C(OCC)(=O)C>[NH2:2][CH2:3][CH2:4][CH:5]=[C:6]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]1[Br:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 14151575100746-87-0

Product 1

HCID 54324149HCID 54324149, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 20 g of 4-(3-aminopropyl)-6-methoxy-2H-[1]-benzopyran hydrochloride in 200 ml of ethyl acetate is added 12.5 g of bromine at room temperature. After 15 minutes at room temperature 24 g of triethylamine is added to yield 4-(3-aminopropylidene)-3-bromo-6-methoxy-2H-[1]-benzopyran and the reaction mixture is refluxed for 2 hours. After washing with water and drying the solvent is removed in vacuo. The residue is dissolved in ethanol and acidified with ethanolic hydrogen chloride to afford 9-methoxy-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 285°-286°.

Sources & evidence

ORD record
ord-9bb25e0f924d4f5da94e18de8130ef87
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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