Dimethylformamide dimethyl acetal → 6-Benzyloxy-3-(dimethylamino-methyleneamino)-7-methoxy-naphthalene-2-carboxylic acid tert-butyl ester

HRID 989369Notes

Reaction equation

HRID 989369 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH:31](OC)[N:32]([CH3:34])[CH3:33]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1[C:17]([N:18]=[CH:31][N:32]([CH3:34])[CH3:33])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 10156578HCID 10156578, compound

Product 1

HCID 113164686-Benzyloxy-3-(dimethylamino-methyleneamino)-7-methoxy-naphthalene-2-carboxylic acid tert-butyl esterYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a round bottom flask containing 10 mL of toluene is added 3-amino-6-benzyloxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester (3.0 g, 7.9 mmol) and dimethylformamide dimethyl acetal (5.4 mL, 31.6 mmol) under a positive nitrogen flow. The mixture is stirred at 120° C. for 1.5 hour, then cooled to room temperature. The volatiles are removed under reduced pressure and the resulting residue dried in vacuo for 15 h to yield 3.0 g of 6-benzyloxy-3-(dimethylamino-methyleneamino)-7-methoxy-naphthalene-2-carboxylic acid tert-butyl ester as a dark oil.

Workup

  1. temperaturecooled to room temperature
  2. customThe volatiles are removed under reduced pressure
  3. customthe resulting residue dried in vacuo for 15 h

Sources & evidence

ORD record
ord-c5b2c160ce0f434da17d361d81c8bac2
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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