2-Amino-2-methyl-1,3-propanediol → 2-[(5-Naphthacenylmethyl)amino]-2-methyl-1,3-propanediol

HRID 414397Notes

Reaction equation

HRID 414397 reaction equation
[CH:1]1[C:18]2[C:5](=[C:6]([CH:19]=O)[C:7]3[C:16]([CH:17]=2)=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]([CH3:27])([CH2:25][OH:26])[CH2:23][OH:24]>CCO.CCOCC>[CH:1]1[C:18]2[C:5](=[C:6]([CH2:19][NH:21][C:22]([CH3:27])([CH2:25][OH:26])[CH2:23][OH:24])[C:7]3[C:16]([CH:17]=2)=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 111495315-Naphthacenecarboxaldehyde

Product 1

HCID 1493102-[(5-Naphthacenylmethyl)amino]-2-methyl-1,3-propanediolYield 50.1%

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

Using the reductive amination procedure described in Example 1, naphthacene-5-carbaldehyde (3A) and 2-amino-2-methyl-1,3-propanediol (Aldrich) gave 50.1% yield of 2-[(5-naphthacenylmethyl)amino]-2-methyl-1,3-propanediol methanesulfonte, mp 197.5°-199°, (EtOH/Et2O), (C, H, N, S).

Sources & evidence

ORD record
ord-94bca551f50d4e2fb1b6b41871e4a2e0
Source dataset
uspto-grants-1988_12
Patent number
US04791231

Reaction notes

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