Benzenepropanal → HCID 20316901, compound

HRID 596254Notes

Reaction equation

HRID 596254 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[NH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([OH:24])[C:19]=2[OH:23])[CH:14]1[OH:25]>C(O)C>[C:1]1([CH2:7][CH2:8][CH:9]=[N:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:24])[C:19]=3[OH:23])[CH:14]2[OH:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 12353618HCID 12353618, compound

Product 1

HCID 20316901HCID 20316901, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 volume parts of ethanol is dissolved 2 parts of 2-amino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide, followed by the addition of 20 parts of β-phenylpropionaldehyde to produce 2-(3-phenylpropylideneamino)-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene. Using palladium-on-carbon as a catalyst, the reaction mixture is subjected to catalytic reduction at ordinary temperature and pressure. After a stoichiometric amount of hydrogen has been absorbed, the reaction mixture is filtered to remove the catalyst and, then, 5000 volume parts of ethyl ether is added to the filtrate. The procedure yields 2 parts of 2-(3-phenylpropylamino)-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide as white crystals melting at 136°-139° C (decomposition).

Sources & evidence

ORD record
ord-719e5b2e37dd4e789c361fd5c0e91a9d
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

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