1-Naphthaldehyde → HCID 69609814, compound

HRID 1245111Notes

Reaction equation

HRID 1245111 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[C:13]1([CH:23]=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH2:23][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69609814HCID 69609814, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Amino-5-chlorobenzoic acid methyl ester (1.85 g, 10.0 mmol) was treated with 1-napthaldehyde (1.56 g, 10.0 mmol) and sodium triacetoxyborohydride (4.23 g, 20.0 mmol) in 1,2-dichloroethane as described in general procedure E to give 5-chloro-2-[(napthalen-1yl-methyl)-amino]-benzoic acid methyl ester (2.54 g, 78%). This methyl ester (2.0 g, 6.13 mmol) was treated with LiOH (2 eq, 1N aqueous solution) according to the general procedure C gave 5-chloro-2-[(napthalen-1yl-methyl)-amino]-benzoic acid (1.64 g, 86.0%).

Sources & evidence

ORD record
ord-197e44a09fbf424a95e7bd4ad1afa332
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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