Benzenepropanal → HCID 20316901, compound

HRID 2419088Notes

Reaction equation

HRID 2419088 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-22f3712b7e4d45c386da61f8d29bf0f6
Source dataset
uspto-grants-1978_08
Patent number
US04104402

Reaction notes

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